Isoxazoline Derivatives and Their Use as Herbicides

ABSTRACT

Compounds of formula: (I) wherein the substituents are as defined in claim  1 , are suitable for use as herbicides. Also claimed are processes for the preparation of the claimed compounds, a herbicidal composition comprising the claimed compounds, and a method of controlling grasses and weeds using them.

The present invention relates to novel, herbicidal isoxazolinecompounds, to processes for their preparation, to compositionscomprising those compounds, and to their use in controlling weeds,especially in crops of useful plants, or in inhibiting plant growth.

Isoxazoline compounds which display a herbicidal action are described,for example, in WO 01/012613, WO 02/062770, WO 03/000686, WO 04/014138and JP 2005/035924. The preparation of these compounds is also describedin WO 04/013106.

Novel sulfoximine compounds which display herbicidal andgrowth-inhibiting properties have now been found.

The present invention accordingly relates to compounds of formula I

whereinR¹ and R² are each independently of the other hydrogen, C₁-C₁₀alkyl,C₁-C₁₀haloalkyl, C₃-C₈cycloalkyl or C₃-C₈cycloalkyl-C₁-C₃alkyl, orR¹ and R² together with the carbon atom to which they are bonded form aC₃-C₇ring,R³ and R⁴ are each independently of the other hydrogen, C₁-C₁₀alkyl,C₁-C₁₀haloalkyl, C₃-C₈cycloalkyl-C₁-C₁₀alkyl, C₁-C₆alkoxy-C₁-C₁₀alkyl orC₃-C₈cycloalkyl, orR³ and R⁴ together with the carbon atom to which they are bonded form aC₃-C₇ring, orR¹ with R³ or R⁴ and together with the carbon atoms to which they arebonded form a C₅-C₈ring, orR² with R³ or R⁴ and together with the carbon atoms to which they arebonded form a C₅-C₈ring;R⁵ and R⁶ are each independently of the other hydrogen, C₁-C₆alkyl,C₃-C₆cycloalkyl, 4,5-dihydropyrazole-CH₂—,C₁-C₆alkylcarbonyloxy-C₂-C₆alkenyl-, C₃-C₆cycloalkylcarbonyl,C₁-C₆alkoxy-C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, cyano,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, pyrrolyl-CH₂—, pyrazolyl-CH₂—,triazolyl-CH₂—, imidazolyl-CH₂—, tetrazolyl-CH₂—, indolyl-CH₂—,indazolyl-CH₂—, benzotriazolyl-CH₂—, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₂-C₆alkenyloxy, C₂-C₆alkynyloxy, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, phenylcarbonyl or phenylcarbonyl substituted byone to three R⁹, orR⁵ and R⁶ are each independently of the other phenoxycarbonyl orphenoxycarbonyl substituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other benzyloxycarbonyl orbenzyloxycarbonyl substituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other nitro, formyl, carboxyl,halogen, azido, thiocyanato, tri(C₁-C₆alkyl)silyl,C₁-C₆alkylcarbonyl-C₁-C₂alkyl, C₁-C₆alkoxycarbonyl-C₁-C₂alkyl,cyano-C₁-C₂alkyl, C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl,di-C₁-C₆alkyl-aminocarbonyl-C₁-C₂alkyl, C₁-C₆alkoxy-C₁-C₂alkyl,C₁-C₂alkyl-P(O)(OC₁-C₆alkyl)₂, C₁-C₂alkyl-NO₂, mercapto, phenylthio orphenylthio substituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other pyridylthio,C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylthio-C₁-C₆alkyl,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfinyl-C₁-C₆alkyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkyl-sulfonyl-C₁-C₆alkyl,C₁-C₆alkylsulphonyloxy-C₁-C₆alkyl, benzylsulfonyl or benzylsulfonylsubstituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other phenylsulfinyl orphenylsulfinyl substituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other phenylsulfonyl orphenylsulfonyl substituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other benzyl or benzylsubstituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other benzyloxy or benzyloxysubstituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCHO, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCOO—C₁-C₆alkyl, —NHCONH—C₁-C₆alkyl,—NHCONH—C₁-C₆haloalkyl, —NHSO₂—C₁-C₆alkyl, —NHSO₂—C₁-C₆haloalkyl,—NHSO₂-phenyl or —NHSO₂-phenyl substituted by one to three R⁹, orR⁵ and R⁶ are each independently of the other —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted by one tothree R⁹, orR⁵ and R⁶ are each independently of the other —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted by oneto three R⁹, orR⁵ and R⁶ are each independently of the other —CONR⁷R⁸ wherein R⁷ and R⁸are each independently of the other hydrogen, C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸ together form aC₃-C₈alkylene group which optionally contains one oxygen or sulfur atomor one to two amino or C₁-C₆alkylamino groups, orR⁵ and R⁶ are each independently of the other phenyl or naphthyl, whichis optionally substituted by one to three substituents independentlyselected from C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, benzyloxycarbonyl orbenzyloxycarbonyl substituted by one to three R⁹, nitro, cyano, formyl,carboxyl, halogen, azido, thiocyanato, tri(C₁-C₆alkyl)silyl, mercapto,phenylthio or phenylthio substituted by one to three R⁹, phenylsulfinylor phenylsulfinyl substituted by one to three R⁹, —SF₅, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆alkyl-SO(NH)—,C₁-C₆alkyl-SO(NCH₃), C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, benzylsulfonyl or benzylsulfonyl substituted byone to three R⁹, phenylsulfonyl or phenylsulfonyl substituted by one tothree R⁹, hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, benzyloxy or benzyloxy substituted by one to three R⁹,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by one to three R⁹, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted by oneto three R⁹, or by —CONR⁷R⁸ wherein R⁷ and R⁸ are each independently ofthe other hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenylor phenyl substituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, orR⁷ and R⁸ together form a C₃-C₈alkylene group which optionally containsone oxygen or sulfur atom or one to two amino or C₁-C₆alkylamino groups,orR⁵ and R⁶ are each independently of the other a 5- to 10-memberedheterocycle containing one to three nitrogen, oxygen or sulfur atoms,which is optionally benzo-fused, and which is optionally substituted byone to three substituents independently selected from C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₁-C₆-hydroxyalkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxy-carbonyl, benzyloxycarbonyl or benzyloxycarbonyl substitutedby one to three R⁹, phenylthio or phenylthio substituted by one to threeR⁹, phenylsulfinyl or phenylsulfinyl substituted by one to three R⁹,nitro, cyano, formyl, carboxyl, halogen, azido, thio-cyanato,tri(C₁-C₆alkyl)silyl, mercapto, —SF₅, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by one to three R⁹, phenylsulfonyl orphenylsulfonyl substituted by one to three R⁹, hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by one to three R⁹, benzyloxy orbenzyloxy substituted by one to three R⁹, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted by one tothree R⁹, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by one to three R⁹, or by —CONR⁷R⁸ wherein R⁷and R⁸ are each independently of the other hydrogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸ together form aC₃-C₈alkylene group which optionally contains one oxygen or sulfur atomor one to two amino or C₁-C₆alkylamino groups,R⁵ and R⁶ together with the carbon atom to which they are bonded form a3- to 10-membered ring which optionally contains one to three nitrogen,oxygen or sulfur atoms and which is optionally substituted by one tothree substituents independently selected from C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkenyl, halogen, cyano, nitro, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, phenylcarbonyl orphenylcarbonyl substituted by C₁-C₆haloalkyl, nitro, cyano or byhalogen, orR⁵ and R⁶ together with the carbon atom to which they are bonded form agroup of the formula C═CR¹⁰R¹¹ wherein R¹⁰ and R¹¹ are independentlyselected from hydrogen, C₁-C₆alkyl, C₁-C₆alkoxy, —NH(C₁-C₆alkyl),—N(C₁-C₆alkyl)₂, C₁-C₆alkoxy-C₁-C₂alkyl, C₁-C₆alkylcarbonyloxy,C₁-C₆alkylcarbonyloxy-C₁-C₂alkyl, C₁-C₆alkoxy-C₁-C₂alkylcarbonyloxy orC₁-C₆alkylcarbonyloxy-C₁-C₂alkylcarbonyloxy;m is 0 or 1;n is 0, 1 or 2;Q is hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxycarbonyl,tri(C₁-C₆alkyl)silyl-ethyloxycarbonyl, C₁-C₆haloalkoxycarbonyl, cyano,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆cycloalkylcarbonyl, phenylcarbonyl or phenylcarbonyl substituted byone to three R⁹, orQ is benzylcarbonyl or benzylcarbonyl substituted by one to three R⁹, orQ is pyridylcarbonyl or pyridylcarbonyl substituted by one to three R⁹,orQ is phenoxycarbonyl or phenoxycarbonyl substituted by one to three R⁹,orQ is benzyloxycarbonyl or benzyloxycarbonyl substituted by one to threeR⁹, orQ is nitro, formyl, tri(C₁-C₆alkyl)silyl, C₁-C₆alkylcarbonyl-C₁-C₂alkyl,C₁-C₆alkoxy-carbonyl-C₁-C₂alkyl, cyano-C₁-C₂alkyl,C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl,di-C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl, C₁-C₆alkoxy-C₁-C₂alkyl,C₁-C₂alkyl-P(O)(OC₁-C₆alkyl)₂, C₁-C₂alkyl-NO₂,C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfinyl-C₁-C₆alkyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkyl-sulfonyl, C₁-C₆alkylsulfonyl-C₁-C₆alkyl, benzylsulfonylor benzylsulfonyl substituted by one to three R⁹, orQ is phenylsulfinyl or phenylsulfinyl substituted by one to three R⁹, orQ is phenylsulfonyl or phenylsulfonyl substituted by one to three R⁹, orQ is benzyl or benzyl substituted by one to three R⁹, orQ is —CONH—SO₂—C₁-C₆alkyl or —CONH—SO₂—C₁-C₆haloalkyl, or Q is —CONR⁷R⁸wherein R⁷ and R⁸ are each independently of the other hydrogen,C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, phenyl or phenylsubstituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸together form a C₃-C₈alkylene group which optionally contains one oxygenor sulfur atom or one to two amino or C₁-C₆alkylamino groups, orQ is phenyl or naphthyl, which is optionally substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,benzyloxycarbonyl or benzyloxycarbonyl substituted by one to three R⁹,nitro, cyano, formyl, carboxyl, halogen, azido, thiocyanato,tri(C₁-C₆alkyl)silyl, mercapto, phenylthio or phenylthio substituted byone to three R⁹, phenylsulfinyl or phenylsulfinyl substituted by one tothree R⁹, —SF₅, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆alkyl-SO(NH)—, C₁-C₆alkyl-SO(NCH₃), C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by one to three R⁹, phenylsulfonyl orphenylsulfonyl substituted by one to three R⁹, hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by one to three R⁹, benzyloxy orbenzyloxy substituted by one to three R⁹, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted by one tothree R⁹, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by one to three R⁹, or by —CONR⁷R⁸ wherein R⁷and R⁸ are each independently of the other hydrogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸ together form aC₃-C₈alkylene group which optionally contains one oxygen or sulfur atomor one to two amino or C₁-C₆alkylamino groups, orQ is a 3- to 10-membered heterocycle containing one or more nitrogen,oxygen or sulfur atoms, which is optionally benzo-fused, and which isoptionally substituted by one to three substituents independentlyselected from C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆-hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, benzyloxycarbonyl orbenzyloxycarbonyl substituted by one to three R⁹, phenylthio orphenylthio substituted by one to three R⁹, phenylsulfinyl orphenylsulfinyl substituted by one to three R⁹, nitro, cyano, formyl,carboxyl, halogen, azido, thiocyanato, tri(C₁-C₆alkyl)silyl, mercapto,—SF₅, C₁-C₆alkylthio, C₁-C₆alkyl-sulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkyl-sulfonyl,benzylsulfonyl or benzylsulfonyl substituted by one to three R⁹,phenylsulfonyl or phenylsulfonyl substituted by one to three R⁹,hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, benzyloxy or benzyloxy substituted by one to three R⁹,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂-C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by one to three R⁹, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted by oneto three R⁹, or by —CONR⁷R⁸ wherein R⁷ and R⁸ are each independently ofthe other hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenylor phenyl substituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, orR⁷ and R⁸ together form a C₃-C₈alkylene group which optionally containsone oxygen or sulfur atom or one to two amino or C₁-C₆alkylamino groups;andY is hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, hydroxyl, carboxyl, halogen,azido, thiocyanato, tri(C₁-C₆alkyl)silyl, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, benzylsulfonyl or benzylsulfonylsubstituted by one to three R⁹, orY is phenylsulfonyl or phenylsulfonyl substituted by one to three R⁹, orY is C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, orY is benzyloxy or benzyloxy substituted by one to three R⁹, orY is —CONH—SO₂—C₁-C₆alkyl or —CONH—SO₂—C₁-C₆haloalkyl, orY is phenyl, naphthyl or tetrahydronaphthyl, which is optionallysubstituted by one to three substituents independently selected fromC₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, benzyloxycarbonyl, nitro,cyano, formyl, carboxyl, halogen, azido, thiocyanato,tri(C₁-C₆alkyl)silyl, mercapto, phenylthio, phenylsulfinyl, —SF₅,C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆haloalkyl-sulfinyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,benzylsulfonyl or benzylsulfonyl substituted by one to three R⁹,phenylsulfonyl or phenylsulfonyl substituted by one to three R⁹,hydroxyl, C₁-C₆alkoxy, C₁-C₆alkyloxy-C₁-C₆alkyl-, C₃-C₆cycloalkyloxywherein one of the CH₂ groups is optionally replaced by an oxygen atom,C₂-C₆alkenyloxy, C₂-C₆-alkynyloxy, NHSO₂—C₁-C₆alkyl,NHSO₂—C₁-C₆haloalkyl, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, benzyloxy or benzyloxy substituted by one to three R⁹,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by one to three R⁹, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted by oneto three R⁹, or by —CONR⁷R⁸ wherein R⁷ and R⁸ are each independently ofthe other hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenylor phenyl substituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, orR⁷ and R⁸ form a C₃-C₈alkylene group which optionally contains oneoxygen or sulfur atom or one to two amino or C₁-C₆alkylamino groups, orY is a 5- to 10-membered heterocycle containing one to three nitrogen,oxygen or sulfur atoms, which is optionally benzo-fused, and which isoptionally substituted by one to three substituents independentlyselected from C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl,C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, nitro,cyano, formyl, carboxyl, halogen, azido, thiocyanato,tri(C₁-C₆alkyl)silyl, mercapto, —SF₅, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by one to three R⁹, phenylsulfonyl orphenylsulfonyl substituted by one to three R⁹, hydroxyl, C₁-C₆alkoxy,C₁-C₆alkyloxy-C₁-C₆alkyl-, C₃-C₆cycloalkyloxy wherein one of the CH₂groups is optionally replaced by an oxygen atom, C₂-C₆alkenyloxy,C₂-C₆-alkynyloxy, NHSO₂—C₁-C₆alkyl, NHSO₂—C₁-C₆haloalkyl,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by one to three R⁹, benzyloxy orbenzyloxy substituted by one to three R⁹, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted by one tothree R⁹, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by one to three R⁹, or by —CONR⁷R⁸ wherein R⁷and R⁸ are each independently of the other hydrogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸ together form aC₃-C₈alkylene group which optionally contains one oxygen or sulfur atomor one to two amino or C₁-C₆alkylamino groups;R⁹ are independently of each other C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or halogen;and to N-oxides, salts and optical isomers of compounds of formula I.

The compounds of the invention may contain one or more asymmetric carbonatoms, for example, in the —CR⁵R⁶— group and the —S(O)_(m)NQ group andmay exist as enantiomers (or as pairs of diastereoisomers) or asmixtures of such. Further, when m is 0, the compounds of the inventionare sulfilimines, which can exists in two enantiomeric forms, and theadjacent carbon can also exists in two enantiomeric forms. Compounds ofgeneral formula I can therefore exist as racemates, diastereoisomers, orsingle enantiomers, and the invention includes all possible isomers orisomer mixtures in all proportions. It is to be expected that for anygiven compound, one isomer may be more herbicidal than another.

The S═N bond shown in Formula I can also be represented as S⁺—N⁻ andthere is still some debate in the literature whether the true characterof this bond is a single or double bond. Whichever depiction is used,the actual compound remains the same.

Except where otherwise stated, alkyl groups and alkyl moieties ofalkoxy, alkylthio, etc., suitably contain from 1 to 10, typically from 1to 6, carbon atoms in the form of straight or branched chains. Examplesare methyl, ethyl, n- and iso-propyl and n-, sec-, iso- and tert-butyl.

Except where otherwise stated, cycloalkyl groups and cycloalkyl moietiesof cycloalkoxy, cycloalkyl-alkoxy, etc., suitably contain from 3 to 8,typically from 3 to 6, carbon atoms. Examples are cyclopropyl,cyclobutyl, cyclopentyl and cyclohexyl. The cycloalkyl radicals may bein bi- or tri-cyclic form.

Except where otherwise stated, haloalkyl groups and haloalkyl moietiesof haloalkoxy, haloalkylthio, etc., also suitably contain from 1 to 6,typically from 1 to 4, carbon atoms in the form of straight or branchedchains. Examples are difluoromethyl and 2,2,2-trifluoroethyl.

Except where otherwise stated, hydroxyalkyl groups also suitably containfrom 1 to 6, typically from 1 to 4, carbon atoms in the form of straightor branched chains Examples are 1,2-dihydroxyethyl and 3-hydroxypropyl.

Except where otherwise stated, alkenyl and alkynyl moieties alsosuitably contain from 2 to 6, typically from 2 to 4, carbon atoms in theform of straight or branched chains. Examples are allyl, but-2-enyl,3-methylbut-2-enyl, ethynyl, propargyl and but-2-ynyl.

Except where otherwise stated, haloalkenyl groups and haloalkynyl groupsalso, suitably contain from 2 to 6, typically from 2 to 4, carbon atomsin the form of straight or branched chains. Examples are trifluoroallyland 1-chloroprop-1-yn-3-yl.

Halo includes fluoro, chloro, bromo and iodo. Most commonly is fluoro,chloro or bromo and usually fluoro or chloro.

Except where otherwise stated, alkylene groups suitably contain from 1to 10, typically from 1 to 6, carbon atoms in the form of straight orbranched chains. Examples are methylene, ethylene, n- and iso-propyleneand n-, sec-, iso- and tert-butylene.

Except where otherwise stated, heterocyclic groups suitably are 5- to10-membered rings containing one to three nitrogen, oxygen or sulfuratoms, which may be optionally benzo-fused. Examples are furyl, thienyl,pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl,tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl,1,2,4,5-tetrazinyl, benzofuryl, isobenzofuryl, benzothiophenyl,isobenzothiophenyl, indolyl, isoindolyl, indazolyl, benzimidazolyl,benztriazolyl, benzoxazolyl, 1,2-benzisoxazolyl, 2,1-benzisoxazolyl,benzothiazolyl, 1,2-benzisothiazolyl, 2,1-benzisothiazolyl,1,2,3-benzoxadiazolyl, 2,1,3-benzoxadiazolyl, 1,2,3-benzothiadiazolyl,2,1,3-benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl,phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl, indolizinyl, benzo-1,3-dioxolyl,4H-benzo-1,3-dioxinyl, and 4H-benzo-1,4-dioxinyl groups and, whereappropriate, N-oxides and salts thereof.

The 3- to 10-membered rings which may be present as substituents in thecompounds according to the invention include both carbocyclic andheterocyclic, aromatic and non-aromatic rings. Such rings may be in theform of single rings or in the form of polycyclic rings. They may carryfurther substituents and/or be benzo-fused. There may be mentioned byway of example phenyl, naphthyl, anthryl, indenyl and phenanthrenyl, theabove-mentioned cycloalkyl radicals, and also rings containing oxygen,sulfur or nitrogen atoms, such as tetrahydrofuranyl, tetrahydropyranyl,1,3-dioxolanyl, 1,3-dioxanyl, 1,4-dioxanyl, and morpholinyl, also furyl,thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl,1,2,4,5-tetrazinyl, benzofuryl, isobenzofuryl, benzothiophenyl,isobenzothiophenyl, indolyl, isoindolyl, indazolyl, benzimidazolyl,benztriazolyl, benzoxazolyl, 1,2-benzisoxazolyl, 2,1-benzisoxazolyl,benzothiazolyl, 1,2-benzisothiazolyl, 2,1-benzisothiazolyl,1,2,3-benzoxadiazolyl, 2,1,3-benzoxadiazolyl, 1,2,3-benzothiadiazolyl,2,1,3-benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl,phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl, indolizinyl, benzo-1,3-dioxolyl,4H-benzo-1,3-dioxinyl, and 4H-benzo-1,4-dioxinyl.

Where R⁵ or R⁶ is independently a heterocycle-methyl group, for exampleimidazolyl-CH₂—, the heterocycle is connected to the methyl group by anitrogen.

The invention also includes N-oxides of the compounds of formula I.

The invention relates likewise to the salts which the compounds offormula I are able to form with amines, alkali metal and alkaline earthmetal bases and quaternary ammonium bases.

Among the alkali metal and alkaline earth metal hydroxides as saltformers, special mention should be made of the hydroxides of lithium,sodium, potassium, magnesium and calcium, but especially the hydroxidesof sodium and potassium. The compounds of formula I according to theinvention also include hydrates which may be formed during the saltformation.

Examples of amines suitable for ammonium salt formation include ammoniaas well as primary, secondary and tertiary C₁-C₁₈alkylamines,C₁-C₄hydroxyalkylamines and C₂-C₄alkoxyalkylamines, for examplemethylamine, ethylamine, n-propylamine, isopropylamine, the fourbutylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine,octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine,heptadecylamine, octadecylamine, methylethylamine,methylisopropylaamine, methylhexylamine, methylnonylamine,methylpentadecylamine, methyloctadecylamine, ethylbutylamine,ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine,dimethylamine, diethylamine, di-n-propylamine, diisopropylamine,di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine,diheptylamine, dioctylamine, ethanolamine, n-propanolamine,isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine,N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine,2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine,propylenediamine, trimethylamine, triethylamine, tri-n-propylamine,triisopropylamine, tri-n-butylamine, triisobutylamine,tri-sec-butylamine, tri-n-amylamine, methoxyethylamine andethoxyethylamine; heterocyclic amines such as, for example, pyridine,quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline,quinuclidine and azepine; primary arylamines such as, for example,anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines,phenylenediamines, benzidines, naphthylamines and o-, m- andp-chloroanilines; but especially triethylamine, isopropylamine anddiisopropylamine.

Preferred quaternary ammonium bases suitable for salt formationcorrespond, for example, to the formula [N(R_(a) R_(b)R_(c)R_(d))]OHwherein R_(a), R_(b), R_(c) and R_(d) are each independently of theothers C₁-C₄alkyl. Other suitable tetraalkylammonium bases with otheranions can be obtained, for example, by anion exchange reactions.

Furthermore, this invention relates to compounds of formula I wherein R¹and R² are each independently hydrogen, C₁-C₁₀alkyl, C₁-C₁₀haloalkyl,C₃-C₈cyclo-alkyl or C₃-C₈cycloalkyl-C₁-C₃alkyl, or

R¹ and R² together with the carbon atom to which they are bonded form aC₃-C₇ring,

R³ and R⁴ are each independently hydrogen, C₁-C₁₀alkyl, C₁-C₁₀haloalkyl,C₃-C₈cyclo-alkyl-C₁-C₁₀alkyl, C₁-C₆alkoxy-C₁-C₁₀alkyl orC₃-C₈cycloalkyl, or

R³ and R⁴ together with the carbon atom to which they are bonded form aC₃-C₇ring, or

R¹ with R³ or R⁴ and together with the carbon atoms to which they arebonded form a C₅-C₈ring, or

R² with R³ or R⁴ and together with the carbon atoms to which they arebonded form a C₅-C₈ring,

R⁵ and R⁶ are each independently hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆alkoxy-carbonyl, cyano, C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl,pyrrolyl-CH₂—, pyrazolyl-CH₂—, triazolyl-CH₂—, imidazolyl-CH₂—,tetrazolyl-CH₂—, indolyl-CH₂—, indazolyl-CH₂—, benzo-triazolyl-CH₂—,C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₂-C₆alkenyloxy,C₂-C₆alkynyloxy, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,phenylcarbonyl or phenylcarbonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, or

R₅ and R₆ are each independently phenoxycarbonyl or phenoxycarbonylsubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently benzyloxycarbonyl or benzyloxycarbonylsubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently nitro, formyl, carboxyl, halogen,azido, thiocyanato, tri(C₁-C₆alkyl)silyl, C₁-C₆alkylcarbonyl-C₁-C₂alkyl,C₁-C₆alkoxycarbonyl-C₁-C₂alkyl, cyano-C₁-C₂alkyl,C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl,di-C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl, C₁-C₆alkoxy-C₁-C₂alkyl,C₁-C₂alkyl-P(O)(OC₁-C₆alkyl)₂, C₁-C₂alkyl-NO₂, mercapto, phenylthio orphenylthio substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro,cyano, formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently pyridylthio, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl,C₁-C₆alkylsulfonyl-C₁-C₆alkyl, benzylsulfonyl or benzylsulfonylsubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently phenylsulfinyl or phenylsulfinylsubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently phenylsulfonyl or phenylsulfonylsubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxysubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently benzyl or benzyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, or

R⁵ and R⁶ are each independently benzyloxy or benzyloxy substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, or

R⁵ and R⁶ are each independently —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCHO, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCOO—C₁-C₆alkyl, —NHCONH—C₁-C₆alkyl,—NHCONH—C₁-C₆haloalkyl, —NHSO₂—C₁-C₆alkyl, —NHSO₂—C₁-C₆haloalkyl,—NHSO₂-phenyl or —NHSO₂-phenyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently —OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl,—OCO-phenyl or —OCO-phenyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, or

R⁵ and R⁶ are each independently —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, carboxyl, nitro, cyano or byhalogen, or

R⁵ and R⁶ are each independently —CONR⁷R⁸ wherein R⁷ and R⁸ are eachindependently hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,phenyl or phenyl substituted by C₁-C₆haloalkyl, nitro, cyano or byhalogen, or R⁷ and R⁸ together form a C₃-C₈alkylene group which maycontain one or more oxygen or sulfur atoms or one or more amino oralkylamino groups, or

R⁵ and R⁶ are each independently phenyl or naphthyl, which rings may besubstituted by C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, benzyloxycarbonyl orbenzyloxycarbonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, nitro, cyano, formyl,carboxyl, halogen, azido, thiocyanato, tri(C₁-C₆alkyl)silyl, mercapto,phenylthio or phenylthio substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,phenylsulfinyl or phenylsulfinyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, —SF₅,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆alkyl-SO(NH)—, C₁-C₆alkyl-SO(NCH₃), C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, phenylsulfonyl orphenylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, benzyloxy or benzyloxysubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,carboxyl, nitro, cyano or by halogen, or by —CONR⁷R⁸ wherein R⁷ and R⁸are each independently hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl, phenyl or phenyl substituted by C₁-C₆haloalkyl, nitro,cyano or by halogen, or R⁷ and R⁸ together form a C₃-C₈alkylene groupwhich may contain one or more oxygen or sulfur atoms or one or moreamino or alkylamino groups, or

R⁵ and R⁶ are each independently a 5- to 10-membered heterocyclecontaining one or more nitrogen, oxygen or sulfur atoms, whichheterocycle may be benzo-fused, and which heterocycle may be substitutedby C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₁-C₆-hydroxyalkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, phenylthio, phenylthio substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,phenylsulfinyl, phenylsulfinyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,nitro, cyano, formyl, carboxyl, halogen, azido, thiocyanato,tri(C₁-C₆alkyl)silyl, mercapto, —SF₅, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, phenylsulfonyl orphenylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkyl-sulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, benzyloxy or benzyloxysubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,carboxyl, nitro, cyano or by halogen, or by —CONR⁷R⁹ wherein R⁷ and R⁸are each independently hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl, phenyl or phenyl substituted by C₁-C₆haloalkyl, nitro,cyano or by halogen, or R⁷ and R⁸ together form a C₃-C₈alkylene groupwhich may contain one or more oxygen or sulfur atoms or one or moreamino or alkylamino groups,

R⁵ and R⁶ together with the carbon atom to which they are bonded form a3- to 10-membered ring which may contain one or more nitrogen, oxygen orsulfur atoms and which may be substituted by C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkenyl, halogen, cyano, nitro, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, phenylcarbonyl orphenylcarbonyl substituted by C₁-C₆haloalkyl, nitro, cyano or byhalogen, or

R⁵ and R⁶ together with the carbon atom to which they are bonded form agroup of the formula C═CH₂, C═CH—C₁-C₆alkyl, C═C(halogen)₂,C═CH—N(C₁-C₆alkyl)₂, C═CH—NH(C₁-C₆alkyl) or C═CH—C₁-C₆alkoxy;

m is 0 or 1;

n is 0, 1 or 2;

Q is hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxycarbonyl,tri(C₁-C₆alkyl)silylethyloxycarbonyl, C₁-C₆haloalkoxycarbonyl, cyano,C₁-C₆haloalkyl, C₁-C₆-hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆cycloalkylcarbonyl, phenylcarbonyl or phenylcarbonyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, or,

Q is benzylcarbonyl or benzylcarbonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, or

Q is pyridylcarbonyl or pyridylcarbonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen or

Q is phenoxycarbonyl or phenoxycarbonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, or

Q is benzyloxycarbonyl or benzyloxycarbonyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, or

Q is nitro, formyl, tri(C₁-C₆alkyl)silyl, C₁-C₆alkylcarbonyl-C₁-C₂alkyl,C₁-C₆alkoxycarbonyl-C₁-C₂alkyl, cyano-C₁-C₂alkyl,C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl,di-C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl, C₁-C₆alkoxy-C₁-C₂alkyl,C₁-C₂alkyl-P(O)(OC₁-C₆alkyl)₂, C₁-C₂alkyl-NO₂,C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfinyl-C₁-C₆alkyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkylsulfonyl-C₁-C₆alkyl, benzylsulfonyl orbenzylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, or

Q is phenylsulfinyl or phenylsulfinyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, or

Q is phenylsulfonyl or phenylsulfonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, or

Q is benzyl or benzyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen, or

Q is —CONE-SO₂—C₁-C₆alkyl or —CONH—SO₂—C₁-C₆haloalkyl, or Q is —CONR⁷R⁸wherein

R⁷ and R⁸ are each independently hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, phenyl or phenyl substituted by C₁-C₆haloalkyl, nitro,cyano or by halogen, or R⁷ and R⁸ together form a C₃-C₈alkylene groupwhich may contain one or more oxygen or sulfur atoms or one or moreamino or alkylamino groups, or

Q is phenyl or naphthyl, which rings may be substituted by C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,benzyloxycarbonyl or benzyloxycarbonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,nitro, cyano, formyl, carboxyl, halogen, azido, thiocyanato,tri(C₁-C₆alkyl)silyl, mercapto, phenylthio or phenylthio substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, phenylsulfinyl or phenylsulfinyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, —SF₅, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆alkyl-SO(NH)—, C₁-C₆alkyl-SO(NCH₃),C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,benzylsulfonyl or benzylsulfonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,phenylsulfonyl or phenylsulfonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, benzyloxy or benzyloxy substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, carboxyl, nitro, cyano or byhalogen, or by —CONR⁷R⁸ wherein R⁷ and R⁸ are each independentlyhydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl or phenylsubstituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸together form a C₃-C₈alkylene group which may contain one or more oxygenor sulfur atoms or one or more amino or alkylamino groups, or

Q is a 3- to 10-membered heterocycle containing one or more nitrogen,oxygen or sulfur atoms, which heterocycle may be benzo-fused, and whichheterocycle may be substituted by C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, C₁-C₆-hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,benzyloxycarbonyl, benzyloxycarbonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,phenylthio, phenylthio substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,phenylsulfinyl, phenylsulfinyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,nitro, cyano, formyl, carboxyl, halogen, azido, thiocyanato,tri(C₁-C₆alkyl)silyl, mercapto, —SF₅, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, phenylsulfonyl orphenylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, benzyloxy or benzyloxysubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or, —OCO-phenyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,carboxyl, nitro, cyano or by halogen, or by —CONR⁷R⁸ wherein R⁷ and R⁸are each independently hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl, phenyl or phenyl substituted by C₁-C₆haloalkyl, nitro,cyano or by halogen, or R⁷ and R⁸ together form a C₃-C₈alkylene groupwhich may contain one or more oxygen or sulfur atoms or one or moreamino or alkylamino groups; and

Y is hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, hydroxyl, carboxyl, halogen,azido, thiocyanato, tri(C₁-C₆alkyl)silyl, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, benzylsulfonyl or benzylsulfonylsubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, carboxyl, nitro,cyano or by halogen, or

Y is phenylsulfonyl or phenylsulfonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, carboxyl, nitro, cyano or by halogen, or

Y is C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, carboxyl, nitro, cyano or byhalogen, or

Y is benzyloxy or benzyloxy substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, carboxyl, nitro, cyano or by halogen, or

Y is —CONH—SO₂—C₁-C₆alkyl or —CONH—SO₂—C₁-C₆haloalkyl, or

Y is phenyl, naphthyl or tetrahydronaphthyl, which rings may besubstituted by C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl,C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl,benzyloxycarbonyl, nitro, cyano, formyl, carboxyl, halogen, azido,thiocyanato, tri(C₁-C₆alkyl)silyl, mercapto, phenylthio, phenylsulfinyl,—SF₅, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,benzylsulfonyl or benzylsulfonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,phenylsulfonyl or phenylsulfonyl substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, benzyloxy or benzyloxy substituted by C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl or by halogen,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, carboxyl, nitro, cyano or byhalogen, or by —CONR⁷R⁸ wherein R⁷ and R⁸ are each independentlyhydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl or phenylsubstituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸form a C₃-C₈alkylene group which may contain one or more oxygen orsulfur atoms or one or more amino or alkylamino groups, or

Y is a 5- to 10-membered heterocycle containing one or more nitrogen,oxygen or sulfur atoms, which heterocycle may be benzo-fused, and whichheterocycle may be substituted by C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl, halogen, azido,thiocyanato, tri(C₁-C₆alkyl)silyl, mercapto, —SF₅, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, phenylsulfonyl orphenylsulfonyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,nitro, cyano, formyl, carboxyl or by halogen, benzyloxy or benzyloxysubstituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano,formyl, carboxyl or by halogen, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted byC₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl orby halogen, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl,carboxyl, nitro, cyano or by halogen, or by —CONR⁷R⁸ wherein R⁷ and R⁸are each independently hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl, phenyl or phenyl substituted by C₁-C₆haloalkyl, nitro,cyano or by halogen, or R⁷ and R⁸ together form a C₃-C₈alkylene groupwhich may contain one or more oxygen or sulfur atoms or one or moreamino or alkylamino groups,

and to N-oxides, salts and optical isomers of compounds of formula I.

Alkyl and alkoxy radicals appearing in the substituent definitions are,for example, methyl, methoxy, ethyl, ethoxy, propyl, propoxy, butyl,butoxy, hexyl, hexyloxy, nonyl, nonyloxy and decyl and decyloxy and alsobranched isomers thereof. Suitable alkenyl and alkynyl radicals arederived from the mentioned alkyl radicals. Cycloalkyl radicals aregenerally cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyland cyclooctyl. The cycloalkyl radicals may be in bi- or tri-cyclicform. Phenyl radicals may be in substituted form. For example, Y may bea phenyl radical which can be substituted, for example, by alkoxy or byalkoxy substituted by halogen etc. The 3- to 10-membered rings which maybe present as substituents in the compounds according to the inventioninclude both carbocyclic and heterocyclic, aromatic and non-aromaticrings. Such rings may be in the form of single rings or in the form ofpolycyclic rings. They may carry further substituents and/or bebenzo-fused. There may be mentioned by way of example phenyl, naphthyl,anthryl, indenyl and phenanthrenyl, the above-mentioned cycloalkylradicals, and also rings containing oxygen, sulfur or nitrogen atoms,such as 1,3-dioxalanyl, dihydro-1,3-dioxolyl, tetrahydrofuranyl andmorpholinyl, also furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, dihydroisoxazolyl, 1,2,3-thiadiazolyl,1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl,pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, tetrazolyl, tetrazinyl, benzofuryl, benzisofuryl,benzothienyl, benzisothienyl, indolyl, benzimidazolyl,2,1,3-benzoxadiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl,quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl,pteridinyl and indolizinyl.

The invention also includes N-oxides of the compounds of formula I.

The invention also includes the optical isomers of the compounds offormula I, especially those which have a chiral carbon atom in the—CR⁵R⁶— group and the —S(O)_(m)NQ group. TABLE 1 Compounds of formulaI.1 I.1

R¹ R² R³ R⁴ R⁵ R⁶ m Q Me Me H H Br CF₃ 1 H Me Me H H CO₂Me F 0 H Me Me HH CN I 1 H Me Me H H Br I 0 H CH₂Cl Me H H Me I 1 H CH₂Cl Me H H CNCO₂Me 1 H CH₂Cl Me H H H I 0 H Me Me H H Br Cl 1 H Me Me H H CN Br 1 HCH₂Cl Me H H CO₂Me Br 0 H CH₂Cl Me H H CN F 1 H Me Me H H CO₂Me I 0 HCH₂Cl Me H H Me F 0 H CH₂Cl Me H H Br Br 0 H CH₂Cl Me H H H CO₂Me 0 HCH₂Cl Me H H H Br 1 H Me Me H H H Br 1 H Me Me H H Br Br 1 H Me Me H H HCF₃ 1 H CH₂Cl Me H H H H 1 H CH₂Cl Me H H CO₂Me I 0 H Me Me H H Me I 1 HCH₂Cl Me H H F CF₃ 1 H CH₂Cl Me H H CO₂Me F 1 H Me Me H H I I 0 H Me MeH H Me Br 1 H Me Me H H I CF₃ 0 H Me Me H H H Br 0 H CH₂Cl Me H H H Br 0H CH₂Cl Me H H Me CF₃ 1 H Me Me H H Br F 0 H Me Me H H F I 1 H Me Me H HBr F 1 H Me Me H H H H 1 H CH₂Cl Me H H CN CF₃ 1 H CH₂Cl Me H H CO₂Me Cl1 H Me Me H H CO₂Me I 1 H Me Me H H H H 0 H CH₂Cl Me H H Me F 1 H CH₂ClMe H H I I 1 H Me Me H H Me CF₃ 0 H Me Me H H F F 1 H CH₂Cl Me H H BrCF₃ 0 H CH₂Cl Me H H Me CN 0 H Me Me H H Me I 0 H Me Me H H CO₂Me F 1 HCH₂Cl Me H H Me Cl 0 H CH₂Cl Me H H CN CN 1 H Me Me H H Me CF₃ 1 H CH₂ClMe H H Br Cl 1 H Me Me H H H Me 1 H Me Me H H CN CO₂Me 1 H Me Me H H CNCN 0 H Me Me H H F F 0 H Me Me H H CO₂Me Cl 1 H CH₂Cl Me H H Br I 1 H MeMe H H Me CO₂Me 0 H Me Me H H H Cl 1 H CH₂Cl Me H H Cl F 0 H CH₂Cl Me HH CN CF₃ 0 H CH₂Cl Me H H Cl I 0 H CH₂Cl Me H H F I 0 H CH₂Cl Me H H HCN 0 H CH₂Cl Me H H Me Br 0 H Me Me H H Cl F 1 H CH₂Cl Me H H Me CO₂Me 1H CH₂Cl Me H H Me Cl 1 H CH₂Cl Me H H CO₂Me CF₃ 1 H CH₂Cl Me H H Me CF₃0 H CH₂Cl Me H H CN Cl 0 H CH₂Cl Me H H I CF₃ 1 H Me Me H H H CO₂Me 1 HCH₂Cl Me H H Cl Cl 0 H CH₂Cl Me H H CO₂Me Cl 0 H Me Me H H H F 1 H CH₂ClMe H H F F 1 H CH₂Cl Me H H Br F 1 H CH₂Cl Me H H Br CF₃ 1 H CH₂Cl Me HH CF₃ CF₃ 0 H CH₂Cl Me H H CN Br 0 H Me Me H H H I 1 H CH₂Cl Me H H CN I0 H Me Me H H Me F 1 H CH₂Cl Me H H Cl CF₃ 0 H Me Me H H Br I 1 H CH₂ClMe H H Br Cl 0 H CH₂Cl Me H H CN CN 0 H Me Me H H Cl CF₃ 1 H CH₂Cl Me HH Cl I 1 H CH₂Cl Me H H CN I 1 H CH₂Cl Me H H I I 0 H Me Me H H Me Me 1H CH₂Cl Me H H Me Me 0 H CH₂Cl Me H H H Me 1 H CH₂Cl Me H H H CO₂Me 1 HCH₂Cl Me H H Br F 0 H CH2Cl Me H H CN Br 1 H Me Me H H Me F 0 H Me Me HH CN Br 0 H CH₂Cl Me H H CO₂Me CF₃ 0 H CH₂Cl Me H H Me I 0 H CH₂Cl Me HH CN Cl 1 H Me Me H H F I 0 H Me Me H H CN Cl 1 H Me Me H H H F 0 HCH₂Cl Me H H CO₂Me Br 1 H Me Me H H I CF₃ 1 H Me Me H H Me Me 0 H Me MeH H Me CO₂Me 1 H Me Me H H CN CF₃ 1 H Me Me H H CO₂Me CF₃ 0 H Me Me H HCN Cl 0 H CH₂Cl Me H H CO₂Me I 1 H CH₂Cl Me H H CN F 0 H CH₂Cl Me H H FF 0 H CH₂Cl Me H H H I 1 H Me Me H H Me CN 1 H CH₂Cl Me H H Cl Cl 1 HCH₂Cl Me H H Cl F 1 H CH₂Cl Me H H H F 1 H Me Me H H CN CO₂Me 0 H Me MeH H Me Cl 0 H Me Me H H CO₂Me Br 0 H CH₂Cl Me H H H CF₃ 0 H CH₂Cl Me H HMe CN 1 H Me Me H H I I 1 H Me Me H H CN CF₃ 0 H CH₂Cl Me H H Br Br 1 HCH₂Cl Me H H Cl CF₃ 1 H CH₂Cl Me H H F I 1 H CH₂Cl Me H H. H CN 1 HCH₂Cl Me H H H CF₃ 1 H Me Me H H H I 0 H Me Me H H CO₂Me CF₃ 1 H CH₂ClMe H H CO₂Me F 0 H Me Me H H CN I 0 H Me Me H H CO₂Me Cl 0 H CH₂Cl Me HH H F 0 H Me Me H H Cl Cl 1 H CH₂Cl Me H H I CF₃ 0 H Me Me H H Cl I 0 HCH₂Cl Me H H F CF₃ 0 H Me Me H H CF₃ CF₃ 0 H Me Me H H CN CN 1 H Me Me HH Br Cl 0 H Me Me H H CN F 0 H Me Me H H Br CF₃ 0 H Me Me H H CN F 1 HMe Me H H H Cl 0 H CH₂Cl Me H H H Cl 1 H Me Me H H H Me 0 H CH₂Cl Me H HMe Me 1 H Me Me H H Cl Cl 0 H Me Me H H F CF₃ 1 H Me Me H H Br Br 0 H MeMe H H H CN 1 H CH₂Cl Me H H H H 0 H Me Me H H Me Br 0 H CH₂Cl Me H HCF₃ CF₃ 1 H Me Me H H Me Cl 1 H CH₂Cl Me H H Br I 0 H Me Me H H Cl I 1 HCH₂Cl Me H H Me CO₂Me 0 H Me Me H H H CF₃ 0 H Me Me H H Me CN 0 H Me MeH H CO₂Me Br 1 H Me Me H H CF₃ CF₃ 1 H CH₂Cl Me H H H Cl 0 H Me Me H HCl CF₃ 0 H CH₂Cl Me H H H Me 0 H Me Me H H Cl F 0 H CH₂Cl Me H H CNCO₂Me 0 H Me Me H H F CF₃ 0 H Me Me H H H CN 0 H Me Me H H H CO₂Me 0 HCH₂Cl Me H H Me Br 1 HTable 2:

Table 2 consists of 176 compounds of general formula I.1, where Q is—COCH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 2 is the same as compound 1 of Table 1except that in compound 1 of Table 2 Q is —COCH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 2 are the same as compounds 2 to176 of Table 1, respectively, except that in the compounds of Table 2 Qis —COCH₃ instead of hydrogen.

Table 3:

Table 3 consists of 176 compounds of general formula I.1, where Q is—CHO, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 3 is the same as compound 1 of Table 1except that in compound 1 of Table 3 Q is —CHO instead of hydrogen.Similarly, compounds 2 to 176 of Table 3 are the same as compounds 2 to176 of Table 1, respectively, except that in the compounds of Table 3 Qis —CHO instead of hydrogen.

Table 4:

Table 4 consists of 176 compounds of general formula I.1, where Q is—CO₂CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 4 is the same as compound 1 of Table 1except that in compound 1 of Table 4 Q is —CO₂CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 4 are the same as compounds 2 to176 of Table 1, respectively, except that in the compounds of Table 4 Qis —CO₂CH₃ instead of hydrogen.

Table 5:

Table 5 consists of 176 compounds of general formula I.1, where Q is—CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 5 is the same as compound 1 of Table 1except that in compound 1 of Table 5 Q is —CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 5 are the same as compounds 2 to176 of Table 1, respectively, except that in the compounds of Table 5 Qis —CH₃ instead of hydrogen.

Table 6:

Table 6 consists of 176 compounds of general formula I.1, where Q is—CN, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed in Table 1.Thus compound 1 of Table 6 is the same as compound 1 of Table 1 exceptthat in compound 1 of Table 6 Q is —CN instead of hydrogen. Similarly,compounds 2 to 176 of Table 6 are the same as compounds 2 to 176 ofTable 1, respectively, except that in the compounds of Table 6 Q is —CNinstead of hydrogen.

Table 7:

Table 7 consists of 176 compounds of general formula I.1, where Q is—NO₂, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 7 is the same as compound 1 of Table 1except that in compound 1 of Table 7 Q is —NO₂ instead of hydrogen.Similarly, compounds 2 to 176 of Table 7 are the same as compounds 2 to176 of Table 1, respectively, except that in the compounds of Table 7 Qis —NO₂ instead of hydrogen.

Table 8:

Table 8 consists of 176 compounds of general formula I.1, where Q is—CO₂ ^(t)Bu, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 8 is the same as compound 1 of Table 1except that in compound 1 of Table 8 Q is —CO₂ ^(t)Bu instead ofhydrogen. Similarly, compounds 2 to 176 of Table 8 are the same ascompounds 2 to 176 of Table 1, respectively, except that in thecompounds of Table 8 Q is —CO₂ ^(t)Bu instead of hydrogen.

Table 9:

Table 9 consists of 176 compounds of general formula I.2, where R¹, R²,R³, R⁴, R⁵, R⁶, m and Q have the values listed in Table 1.

Thus compound 1 of Table 9 is the same as compound 1 of Table 1 exceptthat in compound 1 of Table 9 Y is5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl instead of2,6-difluorophenyl. Similarly, compounds 2 to 176 of Table 9 are thesame as compounds 2 to 176 of Table 1, respectively, except that in thecompounds of Table 9 Y is5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl instead of2,6-difluorophenyl.Table 10:

Table 10 consists of 176 compounds of general formula I.3, where R¹, R²,R³, R⁴, R⁵, R⁶, m and Q have the values listed in Table 1.

Thus compound 1 of Table 10 is the same as compound 1 of Table 1 exceptthat in compound 1 of Table 10 Y is5-fluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl instead of2,6-difluorophenyl. Similarly, compounds 2 to 176 of Table 10 are thesame as compounds 2 to 176 of Table 1, respectively, except that in thecompounds of Table 10 Y is5-fluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl instead of2,6-difluorophenyl.Table 11:

Table 11 consists of 176 compounds of general formula I.4, where R¹, R²,R³R⁴, R⁵, R⁶, m and Q have the values listed in Table 1.

Thus compound 1 of Table 11 is the same as compound 1 of Table 1 exceptthat in compound 1 of Table 11 Y is5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl instead of2,6-difluorophenyl. Similarly, compounds 2 to 176 of Table 11 are thesame as compounds 2 to 176 of Table 1, respectively, except that in thecompounds of Table 11 Y is5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl instead of2,6-difluorophenyl.Table 12:

Table 12 consists of 176 compounds of general formula I.5, where R¹, R²,R³, R⁴, R⁵, R⁶, m and Q have the values listed in Table 1.

Thus compound 1 of Table 12 is the same as compound 1 of Table 1 exceptthat in compound 1 of Table 12 Y is1-methyl-5-trifluormethoxy-3-trifluoromethyl-1H-pyrazol-4-yl instead of2,6-difluorophenyl. Similarly, compounds 2 to 176 of Table 12 are thesame as compounds 2 to 176 of Table 1, respectively, except that in thecompounds of Table 12 Y is1-methyl-5-trifluoromethoxy-3-trifluoromethyl-1H-pyrazol-4-yl instead of2,6-difluorophenyl.Table 13:

Table 13 consists of 176 compounds of general formula I.6, where R¹, R²,R³R⁴, R⁵, R⁶ m and Q have the values listed in Table 1.

Thus compound 1 of Table 13 is the same as compound 1 of Table 1 exceptthat in compound 1 of Table 13 Y is1-methyl-5-(2,2,2-trifluoroethoxy)-3-trifluoromethyl-1H-pyrazol-4-ylinstead of 2,6-difluorophenyl. Similarly, compounds 2 to 176 of Table 13are the same as compounds 2 to 176 of Table 1, respectively, except thatin the compounds of Table 13 Y is1-methyl-5-(2,2,2-trifluoroethoxy)-3-trifluoromethyl-1H-pyrazol-4-ylinstead of 2,6-difluorophenyl.Table 14:

Table 14 consists of 176 compounds of general formula I.7, where R¹, R²,R³, R⁴, R⁵, R⁶, m and Q have the values listed in Table 1.

Thus compound 1 of Table 14 is the same as compound 1 of Table 1 exceptthat in compound 1 of Table 14 Y is1-methyl-5-methylsulfonyloxy-3-trifluoromethyl-1H-pyrazol-4-yl insteadof 2,6-difluorophenyl. Similarly, compounds 2 to 176 of Table 14 are thesame as compounds 2 to 176 of Table 1, respectively, except that in thecompounds of Table 14 Y is1-methyl-5-methylsulfonyloxy-3-trifluoromethyl-1H-pyrazol-4-yl insteadof 2,6-difluorophenyl.Table 15:

Table 15 consists of 176 compounds of general formula I.8, where R¹,R²R³, R⁴, R⁵, R⁶ m and Q have the values listed in Table 1.

Thus compound 1 of Table 15 is the same as compound 1 of Table 1 exceptthat in compound 1 of Table 15 Y is1-methyl-3-trifluoromethyl-5-trifluoromethylsulfonyloxy-1H-pyrazol-4-ylinstead of 2,6-difluorophenyl. Similarly, compounds 2 to 176 of Table 15are the same as compounds 2 to 176 of Table 1, respectively, except thatin the compounds of Table 15 Y is1-methyl-3-trifluoromethyl-5-trifluoromethylsulfonyloxy-1H-pyrazol-4-ylinstead of 2,6-difluorophenyl.Table 16:

Table 16 consists of 176 compounds of general formula 1.2, where Q is—COCH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 16 is the same as compound 1 of Table9 except that in compound 1 of Table 16 Q is —COCH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 16 are the same as compounds 2 to176 of Table 9, respectively, except that in the compounds of Table 16 Qis —COCH₃ instead of hydrogen.

Table 17:

Table 17 consists of 176 compounds of general formula 1.3, where Q is—COCH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 17 is the same as compound 1 of Table10 except that in compound 1 of Table 17 Q is —COCH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 17 are the same ascompounds 2 to 176 of Table 10, respectively, except that in thecompounds of Table 17 Q is —COCH₃ instead of hydrogen.

Table 18:

Table 18 consists of 176 compounds of general formula 1.4, where Q is—COCH₃, and R¹, R², R³, R⁴R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 18 is the same as compound 1 of Table11 except that in compound 1 of Table 18 Q is —COCH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 18 are the same ascompounds 2 to 176 of Table 1, respectively, except that in thecompounds of Table 18 Q is —COCH₃ instead of hydrogen.

Table 19:

Table 19 consists of 176 compounds of general formula I.5, where Q is—COCH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 19 is the same as compound 1 of Table12 except that in compound 1 of Table 19 Q is —COCH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 19 are the same ascompounds 2 to 176 of Table 12, respectively, except that in thecompounds of Table 19 Q is —COCH₃ instead of hydrogen.

Table 20:

Table 20 consists of 176 compounds of general formula I.6, where Q is—COCH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 20 is the same as compound 1 of Table13 except that in compound 1 of Table 20 Q is —COCH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 20 are the same ascompounds 2 to 176 of Table 13, respectively, except that in thecompounds of Table 20 Q is —COCH₃ instead of hydrogen.

Table 21:

Table 21 consists of 176 compounds of general formula I.7, where Q is—COCH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 21 is the same as compound 1 of Table14 except that in compound 1 of Table 21 Q is —COCH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 21 are the same ascompounds 2 to 176 of Table 14, respectively, except that in thecompounds of Table 21 Q is —COCH₃ instead of hydrogen.

Table 22:

Table 22 consists of 176 compounds of general formula I.8, where Q is—COCH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 22 is the same as compound 1 of Table15 except that in compound 1 of Table 22 Q is —COCH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 22 are the same ascompounds 2 to 176 of Table 15, respectively, except that in thecompounds of Table 22 Q is —COCH₃ instead of hydrogen.

Table 23:

Table 23 consists of 176 compounds of general formula I.2, where Q is—CHO, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 23 is the same as compound 1 of Table9 except that in compound 1 of Table 23 Q is —CHO instead of hydrogen.Similarly, compounds 2 to 176 of Table 23 are the same as compounds 2 to176 of Table 9, respectively, except that in the compounds of Table 23 Qis —CHO instead of hydrogen.

Table 24:

Table 24 consists of 176 compounds of general formula I.3, where Q is—CHO, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 24 is the same as compound 1 of Table10 except that in compound 1 of Table 24 Q is —CHO instead of hydrogen.Similarly, compounds 2 to 176 of Table 24 are the same as compounds 2 to176 of Table 10, respectively, except that in the compounds of Table 24Q is —CHO instead of hydrogen.

Table 25:

Table 25 consists of 176 compounds of general formula I.4, where Q is—CHO, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 25 is the same as compound 1 of Table11 except that in compound 1 of Table 25 Q is —CHO instead of hydrogen.Similarly, compounds 2 to 176 of Table 25 are the same as compounds 2 to176 of Table 11, respectively, except that in the compounds of Table 25Q is —CHO instead of hydrogen.

Table 26:

Table 26 consists of 176 compounds of general formula I.5, where Q is—CHO, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 26 is the same as compound 1 of Table12 except that in compound 1 of Table 26 Q is —CHO instead of hydrogen.Similarly, compounds 2 to 176 of Table 26 are the same as compounds 2 to176 of Table 12, respectively, except that in the compounds of Table 26Q is —CHO instead of hydrogen.

Table 27:

Table 27 consists of 176 compounds of general formula I.6, where Q is—CHO, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 27 is the same as compound 1 of Table13 except that in compound 1 of Table 27 Q is —CHO instead of hydrogen.Similarly, compounds 2 to 176 of Table 27 are the same as compounds 2 to176 of Table 13, respectively, except that in the compounds of Table 27Q is —CHO instead of hydrogen.

Table 28:

Table 28 consists of 176 compounds of general formula I.7, where Q is—CHO, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 28 is the same as compound 1 of Table14 except that in compound 1 of Table 28 Q is —CHO instead of hydrogen.Similarly, compounds 2 to 176 of Table 28 are the same as compounds 2 to176 of Table 14, respectively, except that in the compounds of Table 28Q is —CHO instead of hydrogen.

Table 29:

Table 29 consists of 176 compounds of general formula I.8, where Q is—CHO, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 29 is the same as compound 1 of Table15 except that in compound 1 of Table 29 Q is —CHO instead of hydrogen.Similarly, compounds 2 to 176 of Table 29 are the same as compounds 2 to176 of Table 15, respectively, except that in the compounds of Table 29Q is —CHO instead of hydrogen.

Table 30:

Table 30 consists of 176 compounds of general formula I.2, where Q is—CO₂CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 30 is the same as compound 1 of Table9 except that in compound 1 of Table 30 Q is —CO₂CH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 30 are the same ascompounds 2 to 176 of Table 9, respectively, except that in thecompounds of Table 30 Q is —CO₂CH₃ instead of hydrogen.

Table 31:

Table 31 consists of 176 compounds of general formula I.3, where Q is—CO₂CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 31 is the same as compound 1 of Table10 except that in compound 1 of Table 31 Q is —CO₂CH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 31 are the same ascompounds 2 to 176 of Table 10, respectively, except that in thecompounds of Table 31 Q is —CO₂CH₃ instead of hydrogen.

Table 32:

Table 32 consists of 176 compounds of general formula I.4, where Q is—CO₂CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 32 is the same as compound 1 of Table11 except that in compound 1 of Table 32 Q is —CO₂CH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 32 are the same ascompounds 2 to 176 of Table 11, respectively, except that in thecompounds of Table 32 Q is —CO₂CH₃ instead of hydrogen.

Table 33:

Table 33 consists of 176 compounds of general formula I.5, where Q is—CO₂CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 33 is the same as compound 1 of Table12 except that in compound 1 of Table 33 Q is —CO₂CH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 33 are the same ascompounds 2 to 176 of Table 12, respectively, except that in thecompounds of Table 33 Q is —CO₂CH₃ instead of hydrogen.

Table 34:

Table 34 consists of 176 compounds of general formula I.6, where Q is—CO₂CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 34 is the same as compound 1 of Table13 except that in compound 1 of Table 34 Q is —CO₂CH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 34 are the same ascompounds 2 to 176 of Table 13, respectively, except that in thecompounds of Table 34 Q is —CO₂CH₃ instead of hydrogen.

Table 35:

Table 35 consists of 176 compounds of general formula I.7, where Q is—CO₂CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 35 is the same as compound 1 of Table14 except that in compound 1 of Table 35 Q is —CO₂CH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 35 are the same ascompounds 2 to 176 of Table 14, respectively, except that in thecompounds of Table 35 Q is —CO₂CH₃ instead of hydrogen.

Table 36:

Table 36 consists of 176 compounds of general formula I.8, where Q is—CO₂CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 36 is the same as compound 1 of Table15 except that in compound 1 of Table 36 Q is —CO₂CH₃ instead ofhydrogen. Similarly, compounds 2 to 176 of Table 36 are the same ascompounds 2 to 176 of Table 15, respectively, except that in thecompounds of Table 36 Q is —CO₂CH₃ instead of hydrogen.

Table 37:

Table 37 consists of 176 compounds of general formula I.2, where Q is—CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 37 is the same as compound 1 of Table9 except that in compound 1 of Table 37 Q is —CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 37 are the same as compounds 2 to176 of Table 9, respectively, except that in the compounds of Table 37 Qis —CH₃ instead of hydrogen.

Table 38:

Table 38 consists of 176 compounds of general formula I.3, where Q is—CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 38 is the same as compound 1 of Table10 except that in compound 1 of Table 38 Q is —CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 38 are the same as compounds 2 to176 of Table 10, respectively, except that in the compounds of Table 38Q is —CH₃ instead of hydrogen.

Table 39:

Table 39 consists of 176 compounds of general formula I.4, where Q is—CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 39 is the same as compound 1 of Table11 except that in compound 1 of Table 39 Q is —CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 39 are the same as compounds 2 to176 of Table 11, respectively, except that in the compounds of Table 39Q is —CH₃ instead of hydrogen.

Table 40:

Table 40 consists of 176 compounds of general formula I.5, where Q is—CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 40 is the same as compound 1 of Table12 except that in compound 1 of Table 40 Q is —CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 40 are the same as compounds 2 to176 of Table 12, respectively, except that in the compounds of Table 40Q is —CH₃ instead of hydrogen.

Table 41:

Table 41 consists of 176 compounds of general formula I.6, where Q is—CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 41 is the same as compound 1 of Table13 except that in compound 1 of Table 41 Q is —CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 41 are the same as compounds 2 to176 of Table 13, respectively, except that in the compounds of Table 41Q is —CH₃ instead of hydrogen.

Table 42:

Table 42 consists of 176 compounds of general formula I.7, where Q is—CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 42 is the same as compound 1 of Table14 except that in compound 1 of Table 42 Q is —CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 42 are the same as compounds 2 to176 of Table 14, respectively, except that in the compounds of Table 42Q is —CH₃ instead of hydrogen.

Table 43:

Table 43 consists of 176 compounds of general formula I.8, where Q is—CH₃, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 43 is the same as compound 1 of Table15 except that in compound 1 of Table 43 Q is —CH₃ instead of hydrogen.Similarly, compounds 2 to 176 of Table 43 are the same as compounds 2 to176 of Table 15, respectively, except that in the compounds of Table 43Q is —CH₃ instead of hydrogen.

Table 44:

Table 44 consists of 176 compounds of general formula I.2, where Q is—CN, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed in Table 1.Thus compound 1 of Table 44 is the same as compound 1 of Table 9 exceptthat in compound 1 of Table 44 Q is —CN instead of hydrogen. Similarly,compounds 2 to 176 of Table 44 are the same as compounds 2 to 176 ofTable 9, respectively, except that in the compounds of Table 44 Q is —CNinstead of hydrogen.

Table 45:

Table 45 consists of 176 compounds of general formula I.3, where Q is—CN, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed in Table 1.Thus compound 1 of Table 45 is the same as compound 1 of Table 10 exceptthat in compound 1 of Table 45 Q is —CN instead of hydrogen. Similarly,compounds 2 to 176 of Table 45 are the same as compounds 2 to 176 ofTable 10, respectively, except that in the compounds of Table 45 Q is—CN instead of hydrogen.

Table 46:

Table 46 consists of 176 compounds of general formula I.4, where Q is—CN, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed in Table 1.Thus compound 1 of Table 46 is the same as compound 1 of Table 11 exceptthat in compound 1 of Table 46 Q is —CN instead of hydrogen. Similarly,compounds 2 to 176 of Table 46 are the same as compounds 2 to 176 ofTable 11, respectively, except that in the compounds of Table 46 Q is—CN instead of hydrogen.

Table 47:

Table 47 consists of 176 compounds of general formula I.5, where Q is—CN, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed in Table 1.Thus compound 1 of Table 47 is the same as compound 1 of Table 12 exceptthat in compound 1 of Table 47 Q is —CN instead of hydrogen. Similarly,compounds 2 to 176 of Table 47 are the same as compounds 2 to 176 ofTable 12, respectively, except that in the compounds of Table 47 Q is—CN instead of hydrogen.

Table 48:

Table 48 consists of 176 compounds of general formula I.6, where Q is—CN, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed in Table 1.Thus compound 1 of Table 48 is the same as compound 1 of Table 13 exceptthat in compound 1 of Table 48 Q is —CN instead of hydrogen. Similarly,compounds 2 to 176 of Table 48 are the same as compounds 2 to 176 ofTable 13, respectively, except that in the compounds of Table 48 Q is—CN instead of hydrogen.

Table 49:

Table 49 consists of 176 compounds of general formula I.7, where Q is—CN, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed in Table 1.Thus compound 1 of Table 49 is the same as compound 1 of Table 14 exceptthat in compound 1 of Table 49 Q is —CN instead of hydrogen. Similarly,compounds 2 to 176 of Table 49 are the same as compounds 2 to 176 ofTable 14, respectively, except that in the compounds of Table 49 Q is—CN instead of hydrogen.

Table 50:

Table 50 consists of 176 compounds of general formula I.8, where Q is—CN, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed in Table 1.Thus compound 1 of Table 50 is the same as compound 1 of Table 15 exceptthat in compound 1 of Table 50 Q is —CN instead of hydrogen. Similarly,compounds 2 to 176 of Table 50 are the same as compounds 2 to 176 ofTable 15, respectively, except that in the compounds of Table 50 Q is—CN instead of hydrogen.

Table 51:

Table 51 consists of 176 compounds of general formula I.2, where Q is—NO₂, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 51 is the same as compound 1 of Table9 except that in compound 1 of Table 51 Q is —NO₂ instead of hydrogen.Similarly, compounds 2 to 176 of Table 51 are the same as compounds 2 to176 of Table 9, respectively, except that in the compounds of Table 51 Qis —NO₂ instead of hydrogen.

Table 52:

Table 52 consists of 176 compounds of general formula I.3, where Q is—NO₂, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 52 is the same as compound 1 of Table10 except that in compound 1 of Table 52 Q is —NO₂ instead of hydrogen.Similarly, compounds 2 to 176 of Table 52 are the same as compounds 2 to176 of Table 10, respectively, except that in the compounds of Table 52Q is —NO₂ instead of hydrogen.

Table 53:

Table 53 consists of 176 compounds of general formula I.4, where Q is—NO₂, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 53 is the same as compound 1 of Table11 except that in compound 1 of Table 53 Q is —NO₂ instead of hydrogen.Similarly, compounds 2 to 176 of Table 53 are the same as compounds 2 to176 of Table 11, respectively, except that in the compounds of Table 53Q is —NO₂ instead of hydrogen.

Table 54:

Table 54 consists of 176 compounds of general formula I.5, where Q is—NO₂, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 54 is the same as compound 1 of Table12 except that in compound 1 of Table 54 Q is —NO₂ instead of hydrogen.Similarly, compounds 2 to 176 of Table 54 are the same as compounds 2 to176 of Table 12, respectively, except that in the compounds of Table 54Q is —NO₂ instead of hydrogen.

Table 55:

Table 55 consists of 176 compounds of general formula I.6, where Q is—NO₂, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 55 is the same as compound 1 of Table13 except that in compound 1 of Table 55 Q is —NO₂ instead of hydrogen.Similarly, compounds 2 to 176 of Table 55 are the same as compounds 2 to176 of Table 13, respectively, except that in the compounds of Table 55Q is —NO₂ instead of hydrogen.

Table 56:

Table 56 consists of 176 compounds of general formula I.7, where Q is—NO₂, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 56 is the same as compound 1 of Table14 except that in compound 1 of Table 56 Q is —NO₂ instead of hydrogen.Similarly, compounds 2 to 176 of Table 56 are the same as compounds 2 to176 of Table 14, respectively, except that in the compounds of Table 56Q is —NO₂ instead of hydrogen.

Table 57:

Table 57 consists of 176 compounds of general formula I.8, where Q is—NO₂, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 57 is the same as compound 1 of Table15 except that in compound 1 of Table 57 Q is —NO₂ instead of hydrogen.Similarly, compounds 2 to 176 of Table 57 are the same as compounds 2 to176 of Table 15, respectively, except that in the compounds of Table 57Q is —NO₂ instead of hydrogen.

Table 58:

Table 58 consists of 176 compounds of general formula I.2, where Q is—CO₂ ^(t)Bu, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 58 is the same as compound 1 of Table9 except that in compound 1 of Table 58 Q is —CO₂ ^(t)Bu instead ofhydrogen. Similarly, compounds 2 to 176 of Table 58 are the same ascompounds 2 to 176 of Table 9, respectively, except that in thecompounds of Table 58 Q is —CO₂ ^(t)Bu instead of hydrogen.

Table 59:

Table 59 consists of 176 compounds of general formula I.3, where Q is—CO₂ ^(t)Bu, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 59 is the same as compound 1 of Table10 except that in compound 1 of Table 59 Q is —CO₂ ^(t)Bu instead ofhydrogen. Similarly, compounds 2 to 176 of Table 59 are the same ascompounds 2 to 176 of Table 10, respectively, except that in thecompounds of Table 59 Q is —CO₂ ^(t)Bu instead of hydrogen.

Table 60:

Table 60 consists of 176 compounds of general formula I.4, where Q is—CO₂ ^(t)Bu, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 60 is the same as compound 1 of Table11 except that in compound 1 of Table 60 Q is —CO₂ ^(t)Bu instead ofhydrogen. Similarly, compounds 2 to 176 of Table 60 are the same ascompounds 2 to 176 of Table 11, respectively, except that in thecompounds of Table 60 Q is —CO₂ ^(t)Bu instead of hydrogen.

Table 61:

Table 61 consists of 176 compounds of general formula I.5, where Q is—CO₂ ^(t)Bu, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 61 is the same as compound 1 of Table12 except that in compound 1 of Table 61 Q is —CO₂ ^(t)Bu instead ofhydrogen. Similarly, compounds 2 to 176 of Table 61 are the same ascompounds 2 to 176 of Table 12, respectively, except that in thecompounds of Table 61 Q is —CO₂ ^(t)Bu instead of hydrogen.

Table 62:

Table 62 consists of 176 compounds of general formula I.6, where Q is—CO₂ ^(t)Bu, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 62 is the same as compound 1 of Table13 except that in compound 1 of Table 62 Q is —CO₂ ^(t)Bu instead ofhydrogen. Similarly, compounds 2 to 176 of Table 62 are the same ascompounds 2 to 176 of Table 13, respectively, except that in thecompounds of Table 62 Q is —CO₂ ^(t)Bu instead of hydrogen.

Table 63:

Table 63 consists of 176 compounds of general formula I.7, where Q is—CO₂ ^(t)Bu, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 63 is the same as compound 1 of Table14 except that in compound 1 of Table 63 Q is —CO₂ ^(t)Bu instead ofhydrogen. Similarly, compounds 2 to 176 of Table 63 are the same ascompounds 2 to 176 of Table 14, respectively, except that in thecompounds of Table 63 Q is —CO₂ ^(t)Bu instead of hydrogen.

Table 64:

Table 64 consists of 176 compounds of general formula I.8, where Q is—CO₂ ^(t)Bu, and R¹, R², R³, R⁴, R⁵, R⁶ and m have the values listed inTable 1. Thus compound 1 of Table 64 is the same as compound 1 of Table15 except that in compound 1 of Table 64 Q is —CO₂ ^(t)Bu instead ofhydrogen. Similarly, compounds 2 to 176 of Table 64 are the same ascompounds 2 to 176 of Table 15, respectively, except that in thecompounds of Table 64 Q is —CO₂ ^(t)Bu instead of hydrogen.

A group of preferred compounds of formula I comprises those wherein

R¹ and R² are both C₁-C₁₀alkyl;

R³ and R⁴ are both hydrogen;

R⁵ and R⁶ are each independently of the other hydrogen, C₁-C₆alkyl,C₁-C₆alkoxycarbonyl or halogen;

m is 0 or 1;

n is 1;

Q is hydrogen, C₁-C₆alkyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl,C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, phenylcarbonyl orphenylcarbonyl substituted by one to three R⁹, or

Q is pyridylcarbonyl or pyridylcarbonyl substituted by one to three R⁹,or

Q is nitro, formyl, C₁-C₆alkylsulfonyl, or C₁-C₆haloalkylsulfonyl, or

Q is phenylsulfonyl or phenylsulfonyl substituted by one to three R⁹, or

Q is a 3- to 10-membered heterocycle containing one to three nitrogen,oxygen or sulfur atoms, which heterocycle may be benzo-fused, and whichheterocycle may be substituted by C₁-C₆alkyl, C₁-C₆haloalkyl, or cyano;and

Y is phenyl, which is optionally substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, cyano, halogen, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, or phenyl, or

Y is a 5- to 10-membered heterocycle containing one to three nitrogen,oxygen or sulfur atoms, which is optionally substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₁-C₆haloalkyl, orhalogen;

R⁹ are independently of each other nitro or halogen;

and to N-oxides, salts and optical isomers of compounds of formula I.

A group of preferred compounds of formula I comprises those wherein

R¹ and R² are each independently hydrogen, methyl, ethyl, cyclopropyl,cyclobutyl, fluoromethyl, chloromethyl, difluoromethyl ortrifluoromethyl, or

R¹ and R² together with the carbon atom to which they are bonded form aC₃- or C₄-ring,

R³ and R⁴ are each independently hydrogen, methyl, ethyl, cyclopropyl,cyclobutyl, fluoromethyl, chloromethyl, difluoromethyl ortrifluoromethyl, or

R³ and R⁴ together with the carbon atom to which they are bonded form aC₃- or C₄-ring,

or

R¹ with R³ or R⁴ and together with the carbon atoms to which they arebonded form a C₅- or C₆-ring, or

R² with R³ or R⁴ and together with the carbon atoms to which they arebonded form a C₅- or C₆-ring.

A group of especially preferred compounds of formula I comprises thosewherein R¹, R², R³, R⁴ are each independently hydrogen, methyl,fluoromethyl, chloromethyl, difluoromethyl or trifluoromethyl.

A group of preferred compounds of formula I comprises those wherein R¹and R² are both C₁-C₁₀alkyl.

A further group of especially preferred compound of formula I comprisesthose wherein R¹ and R² are both methyl.

Another group of especially preferred compounds of formula I comprisesthose wherein R³ and R⁴ are both hydrogen.

A group of preferred compounds of formula I comprises those wherein Q ishydrogen, C₁-C₆alkyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl,C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, phenylcarbonyl orphenylcarbonyl substituted by one to three R⁹, or

Q is pyridylcarbonyl or pyridylcarbonyl substituted by one to three R⁹,or

Q is nitro, formyl, C₁-C₆alkylsulfonyl, or C₁-C₆haloalkylsulfonyl, or

Q is phenylsulfonyl or phenylsulfonyl substituted by one to three R⁹, or

Q is a 3- to 10-membered heterocycle containing one to three nitrogen,oxygen or sulfur atoms, which heterocycle may be benzo-fused, and whichheterocycle may be substituted by C₁-C₆alkyl, C₁-C₆haloalkyl, or cyano;and

R⁹ are independently of each other nitro or halogen.

A group of especially preferred compounds of formula I comprises thosewherein Q is hydrogen, acetyl, tert-butoxycarbonyl,1-chloroethoxycarbonyl, 4-chlorophenylcarbonyl, 2-chloropyridylcarbonyl,5-cyanopyrimidin-4-yl, ethoxycarbonylmethyl, formyl, methyl,methylsulfonyl, nitro, 4-nitrophenylcarbonyl, 4-nitrophenylsulfonyl,phenylcarbonyl, trimethylsilyl, trifluoroacetyl,4-trifluoromethylpyrimidin-2-yl, trifluoromethylsulfonyl.

A further group of especially preferred compounds of formula I comprisesthose wherein Q is hydrogen, methyl, ethyl, isopropyl, cyano,methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, benzyloxycarbonyl,cyclopropyl, difluoromethyl, trifluoroethyl, vinyl, difluorovinyl,dichlorovinyl, propargyl, acetyl, cyclopropylcarbonyl, benzoyl,benzylcarbonyl, pyridylcarbonyl, trifluoroacetyl, methoxycarbonylethyl,nitro, formyl, trimethylsilyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, cyanomethyl, methylsulfonyl, cyclopropylsulfonyl,benzylsulfonyl, phenylsulfinyl, phenylsulfonyl, trifluoromethylsulfinyl,trifluoromethylsulfonyl, —CONH—SO₂—CH₃, —CONH—SO₂—CF₃, —CONH₂, —CONHCH₃or —CON(CH₃)₂.

A further group of very especially preferred compounds of formula Icomprises those wherein Q is hydrogen, cyano, nitro, formyl, methyl,acetyl, benzylcarbonyl and pyridylcarbonyl, methoxycarbonyl,ethoxycarbonyl, tert-butoxycarbonyl, phenylcarbonyl.

A further group of especially preferred compounds of formula I comprisesthose wherein Q is phenyl or which rings may be substituted by fluorine,chlorine, bromine, iodine, trifluoromethyl, cyclopropyl, methyl,methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio,trifluoromethylsulfinyl, trifluoromethylsulfonyl, methoxy, ethoxy,trifluoromethoxy, difluoromethoxy, cyano, nitro, methoxycarbonyl, —CONH₂or by carboxyl.

A further group of especially preferred compounds of formula I comprisesthose wherein Q is 1,3-dioxalanyl, tetrahydrofuranyl, morpholinyl,furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, tetrazolyl, tetrazinyl, benzofuryl, benzisofuryl,benzothienyl, benzisothienyl, indolyl, benzimidazolyl,2,1,3-benzoxadiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl,quinazolinyl, quinoxalinyl, naphthhydrinyl, benzotriazinyl, purinyl,pteridinyl and indolizinyl, which heterocycles may be substituted byfluorine, chlorine, bromine, iodine, trifluoromethyl, cyclopropyl,methyl, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio,trifluoromethylsulfinyl, trifluoromethylsulfonyl, methoxy, ethoxy,trifluoromethoxy, difluoromethoxy, cyano, nitro, methoxycarbonyl, —CONH₂or by carboxyl.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁵, R⁶, m, n and Y are as defined aboveand Q is hydrogen, formyl or acetyl, most preferably hydrogen.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, m, n and Y are as defined above, R⁵ and R⁶are independently hydrogen, alkoxycarbonyl, alkyl, cyano, halogen orhaloalkyl and Q is hydrogen.

A further group of especially preferred compounds of formula I comprisesthose wherein m is 0 or 1.

A further group of very especially preferred compounds of formula Icomprises those wherein m is 1.

A group of preferred compound of formula I comprises those wherein R⁵and R⁶ are each independently of the other hydrogen, C₁-C₆alkyl, orhalogen.

A group of preferred compound of formula I comprises those wherein R⁵and R⁶ are each independently of the other hydrogen, fluoro, chloro,methyl, acetyl or methoxycarbonyl, preferably hydrogen, fluoro, chloro,or methyl.

A group of especially preferred compounds of formula I comprises thosewherein R⁵ and R⁶ are each independently hydrogen, cyano, methyl, ethyl,isopropyl, methoxycarbonyl, ethoxycarbonyl, benzyloxycarbonyl,cyclopropyl, difluoromethyl, trifluoromethyl, trifluoroethyl,hydroxymethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl,methylsulfonylmethyl, vinyl, difluorovinyl, dichlorovinyl, ethynyl,propargyl, acetyl, trifluoroacetyl, methoxycarbonylethyl, nitro, formyl,bromine, chlorine, fluorine, iodine, azido, trimethylsilyl,methoxycarbonylmethyl, ethoxycarbonylmethyl, cyanomethyl, cyanoethyl,mercapto, phenylthio, methylthio, methylsulfinyl, methylsulfonyl,benzylsulfonyl, phenylsulfinyl, phenylsulfonyl, trifluoromethylthio,trifluoromethylsulfinyl, trifluoromethylsulfonyl, hydroxyl, methoxy,ethoxy, trifluoromethoxy, trifluoroethoxy, methanesulfonyloxy,trifluoro-methanesulfonyloxy, phenoxy, benzyloxy, —CONH—SO₂—CH₃,—CONH—SO₂—CF₃, —NHCO—CH₃, —NHCO—CF₃, —OCO—CH₃, —OCO—CF₃, —OCO-phenyl,—OCONH—CH₃, —OCONH—CH₂CF₃, —OCONH-phenyl, —CONH₂, —CONHCH₃ or—CON(CH₃)₂.

A further group of very especially preferred compounds of formula Icomprises those wherein R⁵ and R⁶ are each independently hydrogen,cyano, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl,benzyloxycarbonyl, cyclopropyl, difluoromethyl, trifluoromethyl,trifluoroethyl, vinyl, difluorovinyl, dichlorovinyl, ethynyl, propargyl,acetyl, trifluoroacetyl, nitro, formyl, bromine, chlorine, fluorine,iodine, azido, trimethylsilyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, cyanomethyl, mercapto, phenylthio, methylthio,methylsulfinyl, methylsulfonyl, benzylsulfonyl, phenylsulfinyl,phenylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl,trifluoromethylsulfonyl, hydroxyl, methoxy, ethoxy, trifluoromethoxy,trifluoroethoxy, methylthiomethyl, methylsulfinylmethyl,methylsulfonylmethyl, methylsulfonyloxy, trifluoromethyl-sulfonyloxy,phenoxy, benzyloxy, —CONH—SO₂—CH₃, —CONH—SO₂—CF₃, —NHCO—CH₃, —NHCO—CF₃,—OCO—CH₃, —OCO—CF₃, —OCO-phenyl, —OCONH—CH₃, —OCONH—CH₂CF₃ or—OCONH-phenyl.

A further group of especially preferred compounds of formula I comprisesthose wherein R⁵ and R⁶ are each independently phenyl or naphthyl, whichrings may be substituted by fluorine, chlorine, bromine, iodine,trifluoromethyl, cyclopropyl, methyl, methylthio, methylsulfinyl,methylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl,trifluoromethylsulfonyl, methoxy, ethoxy, trifluoromethoxy,difluoromethoxy, cyano, nitro, methoxycarbonyl, —CONH₂ or by carboxyl,and R⁶ may additionally be hydrogen, cyano, methyl, ethyl, isopropyl,methoxycarbonyl, ethoxycarbonyl or benzyloxycarbonyl or halogen ortrifluoromethyl.

A further group of very especially preferred compounds of formula Icomprises those wherein R⁵ and R⁶ are each independently phenyl ornaphthyl, which rings may be substituted by fluorine, chlorine,trifluoromethyl, methylsulfonyl, methoxy, trifluoromethoxy, cyano, nitroor by methoxycarbonyl and R⁶ may additionally be hydrogen, cyano,methyl, ethyl, methoxycarbonyl or ethoxycarbonyl or halogen ortrifluoromethyl.

A further group of especially preferred compounds of formula I comprisesthose wherein R⁵ and R⁶ are each independently 1,3-dioxalanyl,tetrahydrofuranyl, morpholinyl, furyl, thienyl, pyrrolyl, pyrazolyl,imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl,pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, tetrazolyl, tetrazinyl, benzofuryl, benzisofuryl,benzothienyl, benzisothienyl, indolyl, benzimidazolyl,2,1,3-benzoxadiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl,quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl,pteridinyl, indolizinyl, dihydroisoxazolyl or a radical of formula

which heterocycles may be substituted by fluorine, chlorine, bromine,iodine, trifluoromethyl, cyclopropyl, methyl, methylthio,methylsulfinyl, methylsulfonyl, trifluoromethylthio,trifluoromethylsulfinyl, trifluoromethylsulfonyl, methoxy, ethoxy,trifluoromethoxy, difluoromethoxy, cyano, nitro, methoxycarbonyl, —CONH₂or by carboxyl, and R₆ may additionally be hydrogen, cyano, methyl,ethyl, isopropyl, methoxycarbonyl, ethoxycarbonyl or benzyloxycarbonylor halogen or trifluoromethyl.

A further group of very especially preferred compounds of formula Icomprises those wherein R⁵ and R⁶ are each independently isothiazolyl,isoxazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, dihydroisoxazolyl or aradical of formula

which rings may be substituted by methyl or methoxy and R⁶ mayadditionally be hydrogen, cyano, methyl, ethyl, methoxycarbonyl orethoxycarbonyl or halogen or trifluoromethyl.

A further group of especially preferred compounds of formula I comprisesthose wherein R⁵ and R⁶ together with the carbon atom to which they arebonded form a cyclopropyl ring which may be substituted by methyl,trifluoromethyl, methoxycarbonyl, ethoxycarbonyl, nitro, vinyl,2-propenyl, acetyl, benzoyl, phenyl, trifluoroacetyl, methylsulfonyl,cyano, chlorine, fluorine, bromine or by methoxy.

A further group of very especially preferred compounds of formula Icomprises those wherein R⁵ and R⁶ together with the carbon atom to whichthey are bonded form a cyclopropyl ring which may be substituted bymethoxycarbonyl, ethoxycarbonyl, cyano, trifluoromethyl, methoxy, nitro,vinyl, bromine, fluorine or by chlorine.

A further group of especially preferred compounds of formula I comprisesthose wherein R⁵ and R⁶ together with the carbon atom to which they arebonded form a 3- to 6-membered heterocycle containing a nitrogen, oxygenor sulfur atom, which heterocycle may be substituted by methyl,trifluoromethyl, methoxycarbonyl, ethoxycarbonyl, trifluoroacetyl,trifluoromethylsulfonyl, methylsulfonyl, acetyl, phenyl, cyano,chlorine, fluorine, bromine or by methoxy.

A further group of especially preferred compounds of formula I comprisesthose wherein R⁵ and R⁶ together with the carbon atom to which they arebonded form a radical of formula C═CH₂, C═CH—CH₃, C═CF₂, C═CCl₂,C═CH—N(CH₃)₂, C═CH—NH(CH₃), C═CH—OCH₃ or C═CH—OC₂H₅.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, Q, m, n and Y are as defined above and R⁵and R⁶ together with the carbon atom to which they are bonded form a 3-to 10-membered ring which may contain one or more nitrogen, oxygen orsulfur atoms, especially a 3- to 6-membered carbocyclic ring, moreespecially cyclopropyl, and which may be substituted by alkyl,haloalkyl, alkoxy, alkoxycarbonyl, halogen, nitro or by cyano.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁶, Q, m, n and Y are as defined above andR⁵ is hydrogen.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, Q, m, n and Y are as defined above and R⁵and R⁶ are both hydrogen.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁶, Q, m, n and Y are as defined above andR⁵ is methoxycarbonyl.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁶, Q, m, n and Y are as defined above andR⁵ is cyano.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁶, Q, m, n and Y are as defined above andR⁵ is methyl.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁶, Q, m, n and Y are as defined above andR⁵ is halogen.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, Q, m, n and Y are as defined above and R⁵and R⁶ are both halogen, preferably independently selected from chlorineand fluorine.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁶, Q, m, n and Y are as defined above andR⁵ is fluorine.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, Q, m, n and Y are as defined above and R⁵and R⁶ are both fluorine.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁶, Q, m, n and Y are as defined above andR⁵ is chlorine.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, Q, m, n and Y are as defined above and R⁵and R⁶ are both chlorine.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, Q, m, n and Y are as defined above and R⁵is fluorine and R⁶ is chlorine.

A further group of especially preferred compounds of formula I comprisesthose wherein R¹, R², R³, R⁴, R⁶, Q, m, n and Y are as defined above andR⁵ is C₁-C₆haloalkyl, especially trifluoromethyl.

A further group of especially preferred compounds of formula I comprisesthose wherein n is 1 or 2.

A further group of very especially preferred compounds of formula Icomprises those wherein n is 1.

A group of preferred compounds of formula I comprises those wherein Y isphenyl, which is optionally substituted by one to three substituentsindependently selected from C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, cyano, halogen, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, or phenyl, or

Y is a 5- to 10-membered heterocycle containing one to three nitrogen,oxygen or sulfur atoms, which is optionally substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₁-C₆haloalkyl, orhalogen.

A group of preferred compounds of formula I comprises those wherein Y isphenyl, which is optionally substituted by one to three substituentsindependently selected from C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, cyano, halogen, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, or phenyl.

A group of preferred compounds of formula I comprises those wherein Y isphenyl optionally substituted by one to three substituents independentlyselected from cyano, difluoromethoxy, ethoxycarbonyl, fluoro,methoxycarbonyl, methyl, methyl-sulfonyl, phenyl, trifluoromethoxy,trifluoromethyl, or trifluoromethylthio.

A group of preferred compounds of formula I comprises those wherein Y is2-biphenyl.

A group of preferred compounds of formula I comprises those wherein Y is2-chloro-3-ethoxycarbonyl-6-methylsulfonylphenyl.

A group of preferred compounds of formula I comprises those wherein Y is2-cyanophenyl.

A group of preferred compounds of formula I comprises those wherein Y is2-difluoromethoxyphenyl.

A group of preferred compounds of formula I comprises those wherein Y is2,3-difluorophenyl.

A group of preferred compounds of formula I comprises those wherein Y is2,4-difluorophenyl.

A group of preferred compounds of formula I comprises those wherein Y is2,5-difluorophenyl.

A group of preferred compounds of formula I comprises those wherein Y is2,6-difluorophenyl.

A group of preferred compounds of formula I comprises those wherein Y is3,5-difluorophenyl.

A group of preferred compounds of formula I comprises those wherein Y is2,6-difluoro-3-tolyl.

A group of preferred compounds of formula I comprises those wherein Y is4-ethoxycarbonyl-2-fluorophenyl.

A group of preferred compounds of formula I comprises those wherein Y is6-fluoro-4H-benzo[1,3]dioxin-8-yl.

A group of preferred compounds of formula I comprises those wherein Y is2-fluoro-4-methoxycarbonylphenyl.

A group of preferred compounds of formula I comprises those wherein Y is2-fluorophenyl.

A group of preferred compounds of formula I comprises those wherein Y is2-fluoro-6-trifluoromethylphenyl.

A group of preferred compounds of formula I comprises those wherein Y isphenyl.

A group of preferred compounds of formula I comprises those wherein Y is2-tolyl.

A group of preferred compounds of formula I comprises those wherein Y is2-trifluoromethoxyphenyl.

A group of preferred compounds of formula I comprises those wherein Y is2-trifluoromethylphenyl.

A group of preferred compounds of formula I comprises those wherein Y is2-trifluoromethylthio.

A group of preferred compounds of formula I comprises those wherein Y isa 5- to 10-membered heterocycle containing one to three nitrogen, oxygenor sulfur atoms, which is optionally substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₁-C₆haloalkyl, orhalogen.

A group of preferred compounds of formula I comprises those wherein Y ispyrazolyl optionally substituted by one to three substituentsindependently selected from difluoromethoxy, difluoromethyl, methoxy,methyl, or trifluoromethyl.

A group of especially preferred compounds of formula I comprises thosewherein Y is pyrazol-4-yl.

A group of preferred compounds of formula I comprises those wherein Y is5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl.

A group of preferred compounds of formula I comprises those wherein Y is3-difluoromethoxy-1-methyl-5-trifluoromethyl-1H-pyrazol-4-yl.

A group of preferred compounds of formula I comprises those wherein Y is1-methyl-3-difluoromethyl-1H-pyrazol-4-yl.

A group of preferred compounds of formula I comprises those wherein Y is1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl.

A further group of especially preferred compounds of formula I comprisesthose wherein Y is phenyl, naphthyl, tetrahydronaphthyl, 1,3-dioxalanyl,tetrahydrofuranyl, morpholinyl, furyl, thienyl, pyrrolyl, pyrazolyl,imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl,pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, tetrazolyl, tetrazinyl, benzofuryl, benzisofuryl,benzothienyl, benzisothienyl, indolyl, benzimidazolyl,2,1,3-benzoxadiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl,quinazolinyl, quinoxalinyl, naphthhydrinyl, benzotriazinyl, purinyl,pteridinyl or indolizinyl, which rings may be substituted by fluorine,chlorine, bromine, iodine, trifluoromethyl, cyclopropyl, methyl,methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio,trifluoromethylsulfinyl, trifluoromethylsulfonyl, methoxy, ethoxy,trifluoroethoxy, trifluoromethoxy, fluoromethoxy, difluoromethoxy,methylsulfonyloxy, trifluoromethylsulfonyloxy, cyano, nitro,methoxycarbonyl, —CONH₂ or by carboxyl.

A further group of very especially preferred compounds of formula Icomprises those wherein Y is phenyl, pyrimidin-5-yl, pyridin-3-yl,isothiazol-4-yl, isoxazol-4-yl, pyrazol-4-yl or thiophen-3-yl, each ofthese groups optionally substituted by halogen, alkyl, haloalkyl,alkoxy, haloalkoxy, alkylsulfonyloxy, haloalkylsulfonyloxy.

1.1) The compounds of formula I, wherein R¹, R², R³, R⁴, R⁵, R⁶, Q, nand Y are as defined above and m is 0 or 1, can be prepared by processesknown per se, e.g. by reacting a compound of formula Ia

wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Y are as defined above and m is 0or 1

1.1A) with compounds of the formulaQ-X^(A)wherein Q is as defined above and X^(A) is a suitable leaving group suchas e.g. a halogen, such as bromide, a carboxylate, such as acetate, analkyl- or aryl-sulfonate, such as p-toluenesulfonate, an imide, such assuccinimide, a sulfonimide, such as bis(phenyl-sulfonyl)imide, or ahaloalkylsulfonate, such as trifluoromethylsulfonate, in the presence ofa base, e.g. a trialkylamine, such as triethylamine, pyridine, an alkalimetal carbonate, such as potassium carbonate or caesium carbonate, analkyl-lithium compound, such as methyl-lithium, n-butyl-lithium andtert-butyl-lithium, a lithium dialkylamide, such as lithiumdiisopropylamide, a metal hydride, preferably an alkali metal hydride,such as sodium hydride, or an alkali metal amide, such as sodium amide,a metal bis(tri(C₁-C₆alkyl)silyl)amide, such as lithiumbis(trimethylsilyl)amide, a metal alkoxide, such as potassiumtert-butoxide, an alkali metal hydroxide or alkaline earth metalhydroxide, such as sodium hydroxide, or a phosphazene base, such asN′-tert-butyl-N,N,N′, N′,N″,N″-hexamethylphosphorimidic triamide(P₁-^(t)Bu),1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-Et),1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi-(phosphazene)(P₂-^(t)Bu),2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine(BEMP) or2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]-undecane(Verkade's base), optionally in the presence of a diluent, e.g.dimethyl-sulfoxide, N,N-dimethylformamide, an ether, such astetrahydrofuran (THF) or 1,2-dimethoxyethane, or a halogenatedhydrocarbon, such as dichloromethane, or mixtures thereof and optionallyin the presence of a catalyst, e.g. a phase transfer catalyst, such astetrabutylammonium bromide or triethylbenzylammonium chloride, or atransition metal catalyst, such as palladium(II) acetate [Pd(OAc)₂] ortris(dibenzylideneacetone)di-palladium(0) [Pd₂(dba)₃], usually in thepresence of a phosphine ligand, such as2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) or triphenylphosphine, or CuI or CuBr in a temperature range of from −120° C. to160° C., preferably from −80° C. to 120° C. Such processes are known inthe literature and are described, for example, in J. Org. Chem., 1993(58) 1922-1923; Tetrahedron Lett., 1996 (37) 3985-3988; J. Org. Chem.,1973 (38) 20-26; Synthesis, 2002 (7) 879-887; Chem. Eur. J. 2001 (7)1118-1128, Org. Lett., 2004 (6) 3293-3296;

1.1B) with compounds of the general formula

wherein Q and R^(B) are C₁-C₆alkyl, such as methyl or ethyl, and X^(B)is a suitable counter ion, such as tetrafluoroborate, in the presence ofa base, e.g. an alkali metal carbonate, such as potassium carbonate orsodium carbonate, and in the presence of a solvent, e.g. a halogenatedhydrocarbon, such as dichloromethane, usually in a temperature rangefrom −50° C. to 30° C. Such processes are known in the literature andare described, for example, in J. Org. Chem., 1978 (43) 4136-4140 and4140-4143; J. Am. Chem. Soc., 1970, 92, 6594;

1.1C) with a formylating agent, e.g. trimethyl orthoformate, optionallyin the presence of an acid, such as p-toluenesulfonic acid, optionallyin the presence of an inert solvent, such as toluene or xylene, usuallyin a temperature range from 0° C. to 200° C., preferably from 50° C. to120° C. Such processes are known in the literature and are described,for example in Tetrahedron Letters, 1987 (36) 4149.

1.1D) with a nitration reagent, e.g. nitric acid, optionally in thepresence of an acid, such as sulfuric acid, optionally in the presenceof an acid anhydride, such as acetic anhydride, optionally in thepresence of an inert solvent, e.g. a halogenated hydrocarbon, such asdichloromethane, in a temperature range from −50° C. to 80° C.,preferably −20° C. to 50° C. Such processes are known in the literatureand are described, for example in Synthesis, 1986 (5) 426-427,Synthesis, 2003 (4) 565-569.

1.2) The compounds of formula Ia, wherein R¹, R², R³, R⁴, R⁵, R⁶, n andY are as defined above and m is 0 or 1, can be prepared by processesknown per se, e.g. by

1.2A) deprotection of a compound of formula Ib

wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Y are as defined above, m is 0 or1 and Q^(A) is an electron withdrawing group, e.g. alkylsulfonyl, suchas methylsulfonyl, arylsulfonyl, such as p-toluenesulfonyl ornitrophenylsulfonyl, or a haloalkylcarbonyl, such astrifluoromethylcarbonyl, or an alkoxycarbonyl, such astert-butoxycarbonyl, or a substituted benzoyl, such as 4-nitrobenzoyl or4-chlorobenzoyl, under acidic conditions, e.g. in the presence of amineral acid, such as sulfuric acid or hydrochloric acid or an organicacid, such as trifluoroacetic acid (J. Am. Chem. Soc., 1973 (95)7418-7423; Chem. Eur. J. 2001 (7) 1118-1128, J. Med. Chem., 2003 (46)4405-4418, J. Org. Chem., 1976 (41) 1728) or under basic conditions,e.g. in the presence of an alkali metal carbonate, such as potassiumcarbonate, or an alkali metal hydroxide, such as sodium hydroxide (Org.Lett., 2004 (8) 1305-1307), or in the presence of a nucleophile, e.g. amercaptan, such as phenylthiol (Tetrahedron Lett., 2002 (43) 2749-2751),in the presence of a diluent, e.g. an ether, such as tetrahydrofuran(THF) or 1,4-dioxane, water, a halogenated hydrocarbon, such asdichloromethane, an alcohol, such as methanol or ethanol, or mixturesthereof, usually in a temperature range of −20° C. to 150° C.,preferably −20° C. to 50° C.;

1.2B) reacting compounds of formula II

wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Y are as defined above and m is 0or 1, with an alkali metal azide, such as sodium azide, under acidicconditions, usually in the presence of sulfuric acid, optionally in thepresence of a solvent, e.g. a halogenated hydrocarbon, such aschloroform or dichloromethane, in a temperature range from −20° C. to50° C., preferably −20° C. to 25° C. (Synthesis, 2003 (4) 565-569; J.Am. Chem. Soc., 1973 (95) 7418), or by reacting withO-mesitylenesulfonylhydroxylamine in the presence of a solvent, e.g. ahalogenated hydrocarbon, such as chloroform or dichloromethane, in atemperature range from −20° C. to 50° C., preferably −20° C. to 25° C.(J. Org. Chem., 1974 (39) 24598-2459; J. Org. Chem., 1973 (38) 1239).

1.3) Compounds of formula Ib, wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Yare as defined above, m is 0 or 1 and Q^(A) is an electron withdrawinggroup, e.g. alkylsulfonyl, such as methylsulfonyl, arylsulfonyl, such asp-toluenesulfonyl or nitrophenylsulfonyl, or a haloalkylcarbonyl, suchas trifluoromethylcarbonyl, or an alkoxycarbonyl, such astert-butoxycarbonyl, can be prepared by processes known per se, byreacting e.g. the compound of formula II (see above) wherein R¹, R², R³,R⁴, R⁵, R⁶, n and Y are as defined above and m is 0 or 1,

1.3A) with an imination reagent of the formulaArI═NQ^(A)wherein Ar is a phenyl group, optionally substituted, e.g. withhalogens, Q^(A) is an electron withdrawing group, e.g. alkylsulfonyl,such as methylsulfonyl, arylsulfonyl, such as p-toluenesulfonyl ornitrophenylsulfonyl, or a haloalkylcarbonyl, such astrifluoromethylcarbonyl, or an alkoxycarbonyl, such astert-butoxycarbonyl, optionally in the presence of a transition metalcatalyst, e.g. Rh₂(OAc)₄, Cu(I)PF₆, Cu(OTf)₂ or CuOTf or AgNO₃,optionally in the presence of a ligand, e.g.4,4′,4″-tri-tert-butyl-2,2′:6′,2″-terpyridine, and in the presence of aninert solvent, such as toluene, dichloromethane or acetonitrile. Theimination reagent ArI═NQ^(A) can be preformed or generated in situ byreacting a compound of the formulaH₂N-Q^(A)with a periodine compound, such as PhI(OAc)₂ or PhI(OCOCF₃)₂, optionallyin the presence of a weak base, such as MgO. Such processes are known inthe literature and are described, for example, in Org. Lett., 2004 (8)1305-1307, Tetrahedron Lett., 1998 (39) 4805, Synthesis, 1999 (7)12512-1260;

1.3B) with an organic azide, such as tert-butoxycarbonyl azide orp-toluene-sulfonyl azide, optionally in the presence of a transitionmetal catalyst, such as FeCl₂, in the presence of a solvent, e.g. ahalogenated hydrocarbon, such as chloroform or dichloromethane, in atemperature range from −20° C. to 50° C., preferably −20° C. to 25° C.(Synthesis, 1999 1251-1260, Tetrahedron Lett., 1998 (39) 5015).

1.4) The compounds of formula II wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Yare as defined above and m is 1 can be prepared by processes known perse by reacting compounds of formula II wherein R¹, R², R³, R⁴, R⁵, R⁶, nand Y are as defined above and m is 0 with a suitable organic orinorganic oxidising agent, e.g. a peroxy acid, such as3-chloroperoxybenzoic acid, peracetic acid or hydrogen peroxide, analkoxyperoxide or a periodate, such as sodium periodiate, optionally inthe presence of a diluent, such as a halogenated hydrocarbon, e.g.dichloromethane or 1,2-dichloroethane, an alcohol, e.g. methanol,N,N-dimethylformamide, water or acetic acid or a mixture thereof. Thereactions are usually carried out in a temperature range of from −80° C.to 120° C., preferably from −20° C. to 50° C. Such processes are knownin the literature and are described e.g. in J. Org. Chem., 2003 (68)3849-3859; J. Med. Chem., 2003 (46) 3021-3032; J. Org. Chem., 2003 (68)500-511; Bioorg. Med. Chem., 1999 (9) 1837-1844.

1.5) The compounds of formula II wherein R¹, R², R³, R⁴, R⁵, R⁶ and Yare as defined above, m is 0, and n is 1, can be prepared, for example,by starting from compounds of formula II wherein R¹, R², R³, R⁴ and Yare as defined above, R⁵ and R⁶ are hydrogen, m is 0, and n is 1, orcompounds of formula II wherein R¹, R², R³, R⁴, R⁵ and Y are as definedabove, R⁶ is hydrogen, m is 0, and n is 1,

by reacting those compounds with a halogenating agent, e.g. bromine oran N-halosuccinimide, such as N-chlorosuccinimide or N-bromosuccinimide,to form compounds of formula II wherein R¹, R², R³, R⁴ and Y are asdefined above, R⁵ is X^(E), and X^(E) in turn is halogen, R⁶ ishydrogen, m is 0, and n is 1, or compounds of formula II wherein R¹, R²,R³, R⁴, R⁵ and Y are as defined above, R⁶ is X^(E), and X^(E) in turn ishalogen, m is 0, and n is 1, respectively, optionally in the presence ofa diluent, e.g. acetic acid or a halogenated hydrocarbon, such as CCl₄or dichloromethane, in a temperature range of from −80° C. to 120° C.,preferably from −20° C. to 60° C.

The compounds of formula II wherein R¹, R², R³, R⁴ and Y are as definedabove, R⁵ is X^(E), and X^(E) in turn is halogen, R⁶ is hydrogen, m is0, and n is 1, or compounds of formula II wherein R¹, R², R³, R⁴, R⁵ andY are as defined above, R⁶ is X^(E), and X^(E) in turn is halogen, m is0, and n is 1, can then be oxidised directly as described above, oralternatively (in a second step) reacted with compounds of formulaM-R⁵ or M-R⁶respectively, wherein R⁵ and R⁶ are as defined above and M-R⁵ or M-R⁶ isa suitable salt or an organometal compound in which M is e.g. Li, MgBr,Na, K or tetraalkylammonium, optionally in the presence of a Lewis acid,e.g. SnCl₄, optionally in the presence of a complexing agent, e.g.hexamethylphosphoramide (HMPA) or1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), andoptionally in the presence of a diluent, e.g. acetonitrile,dichloromethane, diethyl ether or tetrahydrofuran (THF), in atemperature range of from −120° C. to 100° C., preferably from −80° C.to 80° C. Such processes are known in the literature and are described,for example, in J. Org. Chem., 1998 (63) 3706-3716; J. Chem. Soc. PerkinTrans., 1995 (22) 2845-2848; Synthesis 1982 (2), 131-132; LiebigsAnnalen, 1993, 49-54 and Synth. Commun., 1990 (20) 1943-1948.

Compounds of formula II wherein R¹, R², R³, R⁴, n and Y are as definedabove, R⁵ and R⁶ are hydrogen, m is 0, have previously been described inWO 01/012613, WO 03/000686 and WO 04/014138

2) The compounds of formula I, wherein R¹, R², R³, R⁴, R⁵, R⁶, Q, n andY are as defined above and m is 1, can also be prepared by processesknown per se, by reacting e.g. a compound of formula I, wherein R¹, R²,R³, R⁴, R⁵, R⁶, Q, n and Y are as defined above and m is 0, with asuitable organic or inorganic oxidising agent, e.g. a peroxy acid, suchas 3-chloroperoxybenzoic acid, peracetic acid or hydrogen peroxide, or apermanganate, such as potassium permanganate, an alkoxyperoxide or aperiodate, such as sodium periodiate, or a dioxirane, such asdimethyldioxirane, or a hydroperoxide or hypochlorite, such as sodiumhypochlorite, optionally in the presence of a base, e.g. an alkali metalcarbonate, such as potassium carbonate, optionally in the presence of aphase transfer catalyst, such as tetrabutylammonium bromide ortriethylbenzyl ammonium chloride, and in the presence of a solvent, e.g.an alcohol, such as methanol or ethanol, acetone, water, a halogenatedhydrocarbon, such as dichloromethane or chloroform, or mixtures thereof,in a temperature range from −20° C. to 100° C., preferably from −20° C.to 50° C. Such processes are known in the literature and described, forexample in Synthesis, 1982, 77-78; Tetrahedron Lett., 1997 (31)5559-5562; J. Org. Chem., 1979 (44) 2510.

3.1) The compounds of formula I, wherein R¹, R², R³, R⁴, R⁵, R⁶, Q and Yare as defined above, m is 1 and n is 1 can also be prepared byprocesses known per se, e.g. by reacting a compound of formula Ic

wherein R¹, R², R³, R⁴, Q and Y are as defined above and m is 1, in asingle step or stepwise in succession with compounds of the formulaR⁵—X^(A) and/or R⁶—X^(A), wherein R⁵ and R⁶ are as defined above andX^(A) is a suitable leaving group such as e.g. halogen, such as bromide,a carboxylate, such as acetate, an alkyl- or aryl-sulfonate, such asp-toluene-sulfonate, an imide, such as succinimide, a sulfonimide, suchas bis(phenylsulfonyl)-imide, or a haloalkylsulfonate, such astrifluoromethylsulfonate, in the presence of a base, e.g. analkyl-lithium compound, such as methyl-lithium, n-butyl-lithium andtert-butyl-lithium, a lithium dialkylamide, such as lithiumdiisopropylamide, a metal hydride, preferably an alkali metal hydride,such as sodium hydride, or an alkali metal amide, such as sodium amide,a metal bis(tri(C₁-C₆alkyl)silyl)amide, such as lithiumbis(tri-methylsilyl)amide, a metal alkoxide, such as potassiumtert-butoxide, or a phosphazene base, such asN′-tert-butyl-N,N,N′,N′,N″,N″-hexamethylphosphorimidic triamide(P₁-^(t)Bu),1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catena-di(phosphazene)(P₂-Et),1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-^(t)Bu),2-tert-butylimino-2-diethylamino-1,3-di-methyl-perhydro-1,3,2-diazaphosphorine(BEMP) or2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane(Verkade's base), optionally in the presence of a diluent, e.g.N,N-dimethylformamide, an ether, such as tetrahydrofuran (THF) or1,2-dimethoxy-ethane, or a halogenated hydrocarbon, such asdichloromethane, or mixtures thereof and optionally in the presence of acatalyst, e.g. a phase transfer catalyst, such as tetrabutyl-ammoniumbromide or triethylbenzylammonium chloride, or a transition metalcatalyst, such as palladium(II) acetate [Pd(OAc)₂] ortris(dibenzylideneacetone)dipalladium(0) [Pd₂(dba)₃], usually in thepresence of a phosphine ligand, such as2,2′-bis(diphenyl-phosphino)-1,1′-binaphthyl (BINAP) or triphenylphosphine, in a temperature range of from −120° C. to 160° C.,preferably from −80° C. to 120° C. Such processes are known in theliterature and are described, for example, in Eur. J. Org. Chem. 2003(8) 1500-1526, J. Org. Chem., 2002 (67) 2859-2863; Tetrahedron Lett.2000 (41) 2851-2854.

In particular, process 3.1) is useful for the preparation of a compoundof formula I wherein R¹, R², R³, R⁴, Q and Y are as defined above, R⁵ ishalogen, R⁶ is hydrogen or halogen, m is 1 and n is 1, by halogenationof a compound of formula Ic (see above), wherein R¹, R², R³, R⁴, Q and Yare defined as above and m is 1, in a single step or stepwise insuccession with compounds of formula R⁵—X^(A) and/or R⁶—X^(A), whereinR⁵ and/or R⁶ are halogen, e.g. fluorine, chlorine, bromine and iodine,and X^(A) is a suitable leaving group as described above. Preferredreagents are N-fluorobenzenesulfonimide (NFSI) or1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoro-borate) (SELECTFLUOR) for the fluorination,N-chlorosuccinimide (NCS) or hexa-chloroethane for the chlorination,N-bromosuccinimide (NBS) or phenyl trimethylamino tribromide (PTT) forthe bromination, and N-iodosuccinimide (NIS) for the iodination. Thehalogenations are conveniently carried out in an inert solvent,preferably an ether, e.g. THF, and in the presence of a base, preferablyphosphazene bases, e.g.2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine(BEMP), N′-tert-butyl-N,N,N′,N′,N″,N″-hexamethylphosphorimidic triamide(P₁-^(t)Bu),1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-^(t)Bu) or 1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4lambda⁵-5-catena-di(phosphazene) (P₂-Et), or2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]un-decane(Verkade's base), in a temperature range from 0° C. to 50° C.,preferably from 0° C. to 30° C. Alternatively, the halogenations arecarried out in the presence of alkoxide bases, e.g. potassiumtert-butoxide, in the presence of a diluent, preferably an ether, e.g.THF, in a temperature range from −100° C. to 50° C., preferably from−80° C. to 0° C. Alternatively, the halogenations are carried out in thepresence of an alkyl-lithium compound, e.g. n-butyl lithium, in thepresence of a complexing agent, e.g.1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), in thepresence of a diluent, preferably an ether, e.g. THF, in a temperaturerange from −100° C. to 50° C., preferably from −80° C. to 0° C.Alternatively, the halogenations are carried out in the presence of ametal bis(tri(C₁-C₆alkyl)silyl)amide, e.g. sodiumbis(trimethylsilyl)amide, in the presence of a diluent, preferably anether, e.g. THF, in a temperature range from −100° C. to 50° C.,preferably from 80° C. to 0° C.

3.2) The compounds of formula I, wherein R¹, R², R³, R⁴, R⁵, Q and Y areas defined above, R⁶ is C₁-C₁₀alkyl or halogen, m is 1 and n is 1 canalso be prepared by processes known per se, e.g. by reacting a compoundof formula Id

wherein R¹, R², R³, R⁴, Q and Y are defined as above, R⁶ is C₁-C₁₀alkyl,e.g. methyl, or halogen, e.g. chlorine or fluorine, and m is 1 with acompound of formula R⁵—X^(A), wherein R⁵ is as defined above, and X^(A)is suitable leaving group as described above, in the presence of a base,optionally in the presence of a diluent, preferably an inert solvent,and optionally in the presence of a complexing agent in a temperaturerange of from −120° C. to 100° C., preferably from −80° C. to 50° C.

In particular, process 3.2) is useful for the preparation of a compoundof formula I wherein R¹, R², R³, R⁴, Q and Y are as defined above, R⁵ ishalogen, R⁶ is C₁-C₁₀alkyl or halogen, m is 1 and n is 1, byhalogenation of a compound of formula Id (see above) wherein R¹, R², R³,R⁴, Q and Y are defined as above, R⁶ is C₁-C₁₀alkyl, e.g. methyl, orhalogen, e.g. chlorine or fluorine, and m is 1 with a compound offormula R⁵—X^(A), wherein R⁵ is halogen, e.g. fluorine, chlorine,bromine and iodine, and X^(A) is a suitable leaving group as describedabove. Preferred reagents are N-fluorobenzenesulfonimide (NFSI) or1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate) (SELECTFLUOR) for the fluorination,N-chlorosuccinimide (NCS) or hexachloroethane for the chlorination,N-bromosuccinimide (NBS) or phenyl trimethylamino tribromide (PTT) forthe bromination and N-iodosuccinimide (NIS) for the iodination. Thehalogenations are conveniently carried out in an inert solvent,preferably an ether, e.g. THF, and in the presence of a base, preferablyphosphazene bases, e.g.2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine(BEMP), N′-tert-butyl-N,N,N′,N′,N″,N″-hexamethylphosphorimidic triamide(P₁-^(t)Bu),1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-^(t)Bu) or1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-Et), or2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane(Verkade's base), in a temperature range from 0° C. to 50° C.,preferably from 0° C. to 30° C. Alternatively, the halogenations arecarried out in the presence of alkoxide bases, e.g. potassiumtert-butoxide, in the presence of a diluent, preferably an ether, e.g.THF, in a temperature range from −100° C. to 50° C., preferably from−80° C. to 0° C. Alternatively, the halogenations are carried out in thepresence of an alkyl-lithium compound, e.g. n-butyl lithium, in thepresence of a complexing agent, e.g.1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), in thepresence of a diluent, preferably an ether, e.g. THF, in a temperaturerange from −100° C. to 50° C., preferably from −80° C. to 0° C.Alternatively, the halogenations are carried out in the presence of ametal bis(tri(C₁-C₆alkyl)silyl)amide, e.g. sodiumbis(trimethylsilyl)amide, in the presence of a diluent, preferably anether, e.g. THF, in a temperature range from −100° C. to 50° C.,preferably from −80° C. to 0° C.Alternatively, compounds of formula II wherein R¹, R², R³, R⁴, R⁵, R⁶and Y are as defined above, m is 0, and n is 1, can be prepared byreacting a compound of formula VIII wherein R⁵, R⁶ and Y are defined asabove, and X^(F) is a leaving group such as halogen e.g. bromide orchloride, or alkylsulfonate, e.g. methylsulfonate, or arylsulfonate,e.g. tosylate, with thiourea, optionally in the presence of a diluente.g. an alcohol, e.g. ethanol, optionally in the presence of an alkaliiodide, e.g. sodium iodide, potassium iodide, in a temperature range offrom −30° C. to 100° C., preferably from 0° C. to 80° C., to give anisothiourea intermediate of formula XI, which is reacted with a compoundof formula IV

wherein R¹, R²R³ and R⁴ are defined as above, and X^(D) is a suitableleaving group such as halogen, e.g. chloride, an alkyl- or aryl-sulfonylgroup, e.g. methylsulfonyl or phenylsulfonyl, a haloalkylsulfonyl group,e.g. trifluoromethylsulfonyl, or nitro, in the presence of a base, suchas a carbonate, e.g. potassium carbonate, sodium carbonate or potassiumbicarbonate, or a hydroxide, e.g. potassium hydroxide, or an alkoxide,e.g. sodium alkoxide, optionally in the presence of a diluent, such asan alcohol, e.g. ethanol, an ether, e.g. 1,4-dioxane, THF, a polarsolvent, e.g. water, DMF, or a mixture of solvents, e.g. a mixture of1,4-dioxane and water, in a temperature range of from 20° C. to 200° C.,preferably from 50° C. to 150° C., optionally in the presence of aninert gas e.g. nitrogen, and optionally under microwave irradiation.Such processes are known in the literature and are described, forexample, in WO 04/0131106.

A further method of preparing intermediates of formula XI, wherein R⁵,R⁶ and Y are as defined above, is to react a compound of the formula IX,wherein R⁵, R⁶ and Y are defined as above, with thiourea in the presenceof an acid, for example a mineral acid such as hydrochloric acid orhydrobromic acid, or sulfuric acid, or an organic acid such astrifluoroacetic acid, and optionally in the presence of a diluent, suchas an ether, e.g. 1,4-dioxane, THF, a polar solvent, e.g. water, DMF, ora mixture of solvents, e.g. a mixture of 1,4-dioxane and water, in atemperature range of from 20° C. to 270° C., preferably from 20° C. to150° C., optionally under microwave irradiation. Such processes areknown in the literature and are described, for example, in Buchwald andNeilsen, JACS, 110(10), 3171-3175 (1988); Frank and Smith, JACS, 68,2103-2104 (1946); Vetter, Syn. Comm., 28, 3219-3233 (1998).

A further method of preparing compounds of formula II wherein R¹, R²,R³, R⁴, R⁵, R⁶ and Y are as defined above, m is 0, and n is 1, is toreact compound of the formula XII wherein R⁵, R⁶ and Y are as definedabove,

with a compound of formula IV wherein R¹, R², R³ and R⁴ are defined asabove, and X^(D) is a suitable leaving group such as halogen, e.g.chloride, an alkyl- or aryl-sulfonyl group, e.g. methylsulfonyl orphenylsulfonyl, a haloalkylsulfonyl group, e.g.trifluoromethyl-sulfonyl, or nitro, in the presence of a base, e.g.potassium carbonate, optionally in the presence of a diluent e.g. DMF ina temperature range of from 0° C. to 100° C., preferably from 20° C. to50° C. and optionally under an inert atmosphere, e.g. nitrogen. Suchprocesses are known in the literature and are described, for example inWO 01/012613, WO 02/062770 and WO 04/010165.

The compounds of formula Ic and Id, wherein R¹, R², R³, R⁴, R⁶, Q and Yare as defined above and m is 1 can be prepared as described above.

The compounds of formula I according to the invention can be used asherbicides in unmodified form, as obtained in the synthesis, but theyare generally formulated into herbicidal compositions in various waysusing formulation adjuvants, such as carriers, solvents andsurface-active substances. The formulations can be in various physicalforms, e.g. in the form of dusting powders, gels, wettable powders,water-dispersible granules, water-dispersible tablets, effervescentpellets, emulsifiable concentrates, micro-emulsifiable concentrates,oil-in-water emulsions, oil-flowables, aqueous dispersions, oilydispersions, suspo-emulsions, capsule suspensions, emulsifiablegranules, soluble liquids, water-soluble concentrates (with water or awater-miscible organic solvent as carrier), impregnated polymer films orin other forms known e.g. from the Manual on Development and Use of FAOSpecifications for Plant Protection Products, 5th Edition, 1999. Suchformulations can either be used directly or they are diluted prior touse. The dilutions can be made, for example, with water, liquidfertilisers, micronutrients, biological organisms, oil or solvents.

The formulations can be prepared e.g. by mixing the active ingredientwith the formulation adjuvants in order to obtain compositions in theform of finely divided solids, granules, solutions, dispersions oremulsions. The active ingredients can also be formulated with otheradjuvants, such as finely divided solids, mineral oils, oils ofvegetable or animal origin, modified oils of vegetable or animal origin,organic solvents, water, surface-active substances or combinationsthereof. The active ingredients can also be contained in very finemicrocapsules consisting of a polymer. Microcapsules contain the activeingredients in a porous carrier. This enables the active ingredients tobe released into the environment in controlled amounts (e.g.slow-release). Microcapsules usually have a diameter of from 0.1 to 500microns. They contain active ingredients in an amount of about from 25to 95% by weight of the capsule weight. The active ingredients can be inthe form of a monolithic solid, in the form of fine particles in solidor liquid dispersion or in the form of a suitable solution. Theencapsulating membranes comprise, for example, natural or syntheticrubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile,polyacrylate, polyesters, polyamides, polyureas, polyurethane orchemically modified polymers and starch xanthates or other polymers thatare known to the person skilled in the art in this connection.Alternatively, very fine microcapsules can be formed in which the activeingredient is contained in the form of finely divided particles in asolid matrix of base substance, but the microcapsules are not themselvesencapsulated.

The formulation adjuvants that are suitable for the preparation of thecompositions according to the invention are known per se. As liquidcarriers there may be used: water, toluene, xylene, petroleum ether,vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acidanhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone,butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkylesters of acetic acid, diacetone alcohol, 1,2-dichloropropane,diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycolabietate, diethylene glycol butyl ether, diethylene glycol ethyl ether,diethylene glycol methyl ether, N,N-dimethylformamide, dimethylsulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methylether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone,ethyl acetate, 2-ethylhexanol, ethylene carbonate,1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyllactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycolmethyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glyceroldiacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamylacetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene,isopropyl myristate, lactic acid, laurylamine, mesityl oxide,methoxy-propanol, methyl isoamyl ketone; methyl isobutyl ketone, methyllaurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene,n-hexane, n-octylamine, octa-decanoic acid, octylamine acetate, oleicacid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400),propionic acid, propyl lactate, propylene carbonate, propylene glycol,propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate,triethylene glycol, xylenesulfonic acid, paraffin, mineral oil,trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butylacetate, propylene glycol methyl ether, diethylene glycol methyl ether,methanol, ethanol, isopropanol, and alcohols of higher molecular weight,such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol,ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone andthe like. Water is generally the carrier of choice for diluting theconcentrates. Suitable solid carriers are, for example, talc, titaniumdioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr,limestone, calcium carbonate, bentonite, calcium montmorillonite,cottonseed husks, wheat flour, soybean flour, pumice, wood flour, groundwalnut shells, lignin and similar substances, as described, for example,in CFR 180.1001. (c) & (d).

A large number of surface-active substances can advantageously be usedin both solid and liquid formulations, especially in those formulationswhich can be diluted with a carrier prior to use. Surface-activesubstances may be anionic, cationic, non-ionic or polymeric and they canbe used as emulsifiers, wetting agents or suspending agents or for otherpurposes. Typical surface-active substances include, for example, saltsof alkyl sulfates, such as diethanolammonium lauryl sulfate; salts ofalkylarylsulfonates, such as calcium dodecylbenzenesulfonate;alkylphenol/alkylene oxide addition products, such as nonylphenolethoxylate; alcohol/alkylene oxide addition products, such astridecylalcohol ethoxylate; soaps, such as sodium stearate; salts ofalkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate;dialkyl esters of sulfosuccinate salts, such as sodiumdi(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitololeate; quaternary amines, such as lauryltrimethylammonium chloride,polyethylene glycol esters of fatty acids, such as polyethylene glycolstearate; block copolymers of ethylene oxide and propylene oxide; andsalts of mono- and di-alkylphosphate esters; and also further substancesdescribed e.g. in “McCutcheon's Detergents and Emulsifiers Annual” MCPublishing Corp., Ridgewood N.J., 1981.

Further adjuvants that can usually be used in pesticidal formulationsinclude crystallisation inhibitors, viscosity modifiers, suspendingagents, dyes, anti-oxidants, foaming agents, light absorbers, mixingauxiliaries, antifoams, complexing agents, neutralising or pH-modifyingsubstances and buffers, corrosion inhibitors, fragrances, wettingagents, take-up enhancers, micronutrients, plasticisers, glidants,lubricants, dispersants, thickeners, antifreezes, microbicides, and alsoliquid and solid fertilisers.

The compositions according to the invention can additionally include anadditive comprising an oil of vegetable or animal origin, a mineral oil,alkyl esters of such oils or mixtures of such oils and oil derivatives.The amount of oil additive in the composition according to the inventionis generally from 0.01 to 10%, based on the spray mixture. For example,the oil additive can be added to the spray tank in the desiredconcentration after the spray mixture has been prepared. Preferred oiladditives comprise mineral oils or an oil of vegetable origin, forexample rapeseed oil, olive oil or sunflower oil, emulsified vegetableoil, such as AMIGO® (Rhône-Poulenc Canada Inc.), alkyl esters of oils ofvegetable origin, for example the methyl derivatives, or an oil ofanimal origin, such as fish oil or beef tallow. A preferred additivecontains, for example, as active components essentially 80% by weightalkyl esters of fish oils and 15% by weight methylated rapeseed oil, andalso 5% by weight of customary emulsifiers and pH modifiers. Especiallypreferred oil additives comprise alkyl esters of C₈-C₂₂ fatty acids,especially the methyl derivatives of C₁₂-C₁₈ fatty acids, for examplethe methyl esters of lauric acid, palmitic acid and oleic acid, being ofimportance. Those esters are known as methyl laurate (CAS-111-82-0),methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9). Apreferred fatty acid methyl ester derivative is Emery® 2230 and 2231(Cognis GmbH). Those and other oil derivatives are also known from theCompendium of Herbicide Adjuvants, 5th Edition, Southern IllinoisUniversity, 2000.

The application and action of the oil additives can be further improvedby combination with surface-active substances, such as non-ionic,anionic or cationic surfactants. Examples of suitable anionic, non-ionicand cationic surfactants are listed on pages 7 and 8 of WO 97/34485.Preferred surface-active substances are anionic surfactants of thedodecylbenzylsulfonate type, especially the calcium salts thereof, andalso non-ionic surfactants of the fatty alcohol ethoxylate type. Specialpreference is given to ethoxylated C₁₂-C₂₂ fatty alcohols having adegree of ethoxylation of from 5 to 40. Examples of commerciallyavailable surfactants are the Genapol types (Clariant AG). Alsopreferred are silicone surfactants, especially polyalkyl-oxide-modifiedheptamethyltriloxanes which are commercially available e.g. as SilwetL-77® and also perfluorinated surfactants. The concentration of thesurface-active substances in relation to the total additive is generallyfrom 1 to 30% by weight. Examples of oil additives consisting ofmixtures of oil or mineral oils or derivatives thereof with surfactantsare Edenor ME SU®, Turbocharge® (Syngenta AG, CH) or ActipronC (BP OilUK Limited, GB).

If desired, it is also possible for the mentioned surface-activesubstances to be used in the formulations on their own, that is to saywithout oil additives.

Furthermore, the addition of an organic solvent to the oiladditive/surfactant mixture may contribute to an additional enhancementof action. Suitable solvents are, for example, Solvesso® (ESSO) orAromatic Solvent® (Exxon Corporation). The concentration of suchsolvents can be from 10 to 80% by weight of the total weight. Oiladditives that are present in admixture with solvents are described, forexample, in US-A-4,834,908. A commercially available oil additivedisclosed therein is known by the name MERGE® (BASF Corporation). Afurther oil additive that is preferred according to the invention isSCORE® (Syngenta Crop Protection Canada).

In addition to the oil additives listed above, for the purpose ofenhancing the action of the compositions according to the invention itis also possible for formulations of alkylpyrrolidones (e.g. Agrimax®)to be added to the spray mixture. Formulations of synthetic lattices,e.g. polyacrylamide, polyvinyl compounds or poly-1-p-menthene (e.g.Bond®, Courier® or Emerald®) may also be used. It is also possible forsolutions that contain propionic acid, for example EurogkemPen-e-trate®, to be added to the spray mixture as action-enhancingagent.

The herbicidal compositions generally comprise from 0.1 to 99% byweight, especially from 0.1 to 95% by weight, compounds of formula I andfrom 1 to 99.9% by weight of a formulation adjuvant which preferablyincludes from 0 to 25% by weight of a surface-active substance. Whereascommercial products will preferably be formulated as concentrates, theend user will normally employ dilute formulations.

The rates of application of compounds of formula I may vary within widelimits and depend on the nature of the soil, the method of application(pre- or post-emergence; seed dressing; application to the seed furrow;no tillage application etc.), the crop plant, the grass or weed to becontrolled, the prevailing climatic conditions, and other factorsgoverned by the method of application, the time of application and thetarget crop. The compounds of formula I according to the invention aregenerally applied at a rate of from 10 to 2000 g/ha, especially from 50to 1000 g/ha.

Preferred formulations have especially the following compositions(%=percent by weight): Emulsifiable concentrates: active ingredient: 1to 95%, preferably 60 to 90% surface-active agent: 1 to 30%, preferably5 to 20% liquid carrier: 1 to 80%, preferably 1 to 35%

Dusts: active ingredient:  0.1 to 10%, preferably 0.1 to 5% solidcarrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension concentrates: active ingredient:  5 to 75%, preferably 10 to50% water: 94 to 24%, preferably 88 to 30% surface-active agent:  1 to40%, preferably 2 to 30%

Wettable powders: active ingredient: 0.5 to 90%, preferably 1 to 80%surface-active agent: 0.5 to 20%, preferably 1 to 15% solid carrier:   5to 95%, preferably 15 to 90%

Granules: active ingredient:  0.1 to 30%, preferably 0.1 to 15% solidcarrier: 99.5 to 70%, preferably 97 to 85%The following Examples further illustrate, but do not limit, theinvention.

Formulation Examples for Herbicides of Formula I (%=% by Weight) F1.Emulsifiable concentrates a) b) c) d) active ingredient 5% 10% 25% 50%calcium dodecylbenzenesulfonate 6%  8%  6%  8% castor oil polyglycolether 4% —  4%  4% (36 mol of ethylene oxide) octylphenol polyglycolether —  4% —  2% (7-8 mol of ethylene oxide) NMP — — 10% 20% arom.hydrocarbon mixture 85%  78% 55% 16% C₉-C₁₂

Emulsions of any desired concentration can be obtained from suchconcentrates by dilution with water. F2. Solutions a) b) c) d) activeingredient  5% 10% 50% 90% 1-methoxy-3-(3-methoxy- — 20% 20% —propoxy)-propane polyethylene glycol MW 400 20% 10% — — NMP — — 30% 10%arom. hydrocarbon mixture 75% 60% — — C₉-C₁₂

The solutions are suitable for use in the form of microdrops. F3.Wettable powders a) b) c) d) active ingredient 5% 25%  50%  80% sodiumlignosulfonate 4% — 3% — sodium lauryl sulfate 2% 3% —  4% sodiumdiisobutylnaphthalene- — 6% 5%  6% sulfonate octylphenol polyglycolether — 1% 2% — (7-8 mol of ethylene oxide) highly dispersed silicicacid 1% 3% 5% 10% kaolin 88%  62%  35%  —

The active ingredient is mixed thoroughly with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders which can be diluted with water to give suspensions of anydesired concentration. F4. Coated granules a) b) c) active ingredient0.1% 5% 15% highly dispersed silicic acid 0.9% 2% 2% inorganic carrier99.0% 93% 83% (diameter 0.1-1 mm) e.g. CaCO₃ or SiO₂

The active ingredient is dissolved in methylene chloride and applied tothe carrier by spraying, and the solvent is then evaporated off invacuo. F5. Coated granules a) b) c) active ingredient 0.1% 5% 15%polyethylene glycol MW 200 1.0% 2% 3% highly dispersed silicic acid 0.9%1% 2% inorganic carrier 98.0% 92% 80% (diameter 0.1-1 mm) e.g. CaCO₃ orSiO₂

The finely ground active ingredient is uniformly applied, in a mixer, tothe carrier moistened with polyethylene glycol. Non-dusty coatedgranules are obtained in this manner. F6. Extruder granules a) b) c) d)active ingredient 0.1% 3% 5% 15% sodium lignosulfonate 1.5% 2% 3% 4%carboxymethylcellulose 1.4% 2% 2% 2% kaolin 97.0% 93% 90% 79%

The active ingredient is mixed and ground with the adjuvants, and themixture is moistened with water. The mixture is extruded and then driedin a stream of air. F7. Dusts a) b) c) active ingredient 0.1% 1% 5%talcum 39.9% 49% 35% kaolin 60.0% 50% 60%

Ready-to-use dusts are obtained by mixing the active ingredient with thecarriers and grinding the mixture in a suitable mill. F8. Suspensionconcentrates a) b) c) d) active ingredient 3% 10%  25%  50%  ethyleneglycol 5% 5% 5% 5% nonylphenol polyglycol ether — 1% 2% — (15 mol ofethylene oxide) sodium lignosulfonate 3% 3% 4% 5% carboxymethylcellulose1% 1% 1% 1% 37% aqueous formaldehyde 0.2%   0.2%   0.2%   0.2%  solution silicone oil emulsion 0.8%   0.8%   0.8%   0.8%   water 87% 79%  62%  38% The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired concentration can be obtained by dilution with water.

The invention relates also to a method for the selective control ofgrasses and weeds in crops of useful plants, wherein the useful plantsor the area of cultivation or locus thereof is treated with thecompounds of formula I.

Useful plant crops in which the composition according to the inventioncan be used include especially maize, soybeans, cotton, cereals, e.g.wheat and barley, rice, sugar cane, sugar beet, sunflowers and rape.Crops are to be understood as also including those crops which have beenrendered tolerant to herbicides or classes of herbicides (e.g. ALS-,GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods ofbreeding or by genetic engineering. An example of a crop that has beenrendered tolerant to imidazolinones, e.g. imazamox, by conventionalmethods of breeding is Clearfield® summer rape (canola). Examples ofcrops that have been rendered tolerant to herbicides by geneticengineering methods include e.g. glyphosate- and glufosinate-resistantmaize varieties commercially available under the trade namesRoundupReady® and LibertyLink®. The weeds to be controlled may be bothmonocotyledonous and dicotyledonous weeds, for example Stellaria,Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium,Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus,Alopecurus, Sorghum, Rottboellia, Cyperus, Abutilon, Sida, Xanthium,Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola andVeronica.

Crops are also to be understood as being those which have been renderedresistant to harmful insects by genetic engineering methods, for exampleBt maize (resistant to European corn borer), Bt cotton (resistant tocotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).Examples of Bt maize are the Bt 176 maize hybrids of NK® (SyngentaSeeds). The Bt toxin is a protein that is formed naturally by Bacillusthuringiensis soil bacteria. Examples of toxins, or transgenic plantsable to synthesise such toxins, are described in EP-A-451 878, EP-A-374753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examplesof transgenic plants comprising one or more genes that code for aninsecticidal resistance and express one or more toxins are KnockOut®(maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton),NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant crops or seedmaterial thereof can be both resistant to herbicides and, at the sametime, resistant to insect feeding (“stacked” transgenic events). Forexample, seed can have the ability to express an insecticidal Cry3protein while at the same time being tolerant to glyphosate. Crops arealso to be understood as being those which are obtained by conventionalmethods of breeding or genetic engineering and contain so-called outputtraits (e.g. improved storage stability, higher nutritional value andimproved flavour).

Areas under cultivation include land on which the crop plants arealready growing and land intended for cultivation with those cropplants.

The compounds of formula I according to the invention can also be usedin combination with one or more other herbicides. In particular, thefollowing mixtures of the compound of formula I are important:

compound of formula I+acetochlor, compound of formula I+acifluorfen,compound of formula I+acifluorfen-sodium, compound of formulaI+aclonifen, compound of formula I+acrolein, compound of formulaI+alachlor, compound of formula I+alloxydim, compound of formula I+allylalcohol, compound of formula I+ametryn, compound of formulaI+amicarbazone, compound of formula I+amidosulfuron, compound of formulaI+aminopyralid, compound of formula I+amitrole, compound of formulaI+ammonium sulfamate, compound of formula I+anilofos, compound offormula I+asulam, compound of formula I+atraton, compound of formulaI+atrazine, compound of formula I+azimsulfuron, compound of formulaI+BCPC, compound of formula I+beflubutamid, compound of formulaI+benazolin, compound of formula I+benfluralin, compound of formulaI+benfuresate, compound of formula I+bensulfuron, compound of formulaI+bensulfuron-methyl, compound of formula I+bensulide, compound offormula I+bentazone, compound of formula I+benzfendizone, compound offormula I+benzobicyclon, compound of formula I+benzofenap, compound offormula I+bifenox, compound of formula I+bilanafos, compound of formulaI+bispyribac, compound of formula I+bispyribac-sodium, compound offormula I+borax, compound of formula I+bromacil, compound of formulaI+bromobutide, compound of formula I+bromoxynil, compound of formulaI+butachlor, compound of formula I+butafenacil, compound of formulaI+butamifos, compound of formula I+butralin, compound of formulaI+butroxydim, compound of formula I+butylate, compound of formulaI+cacodylic acid, compound of formula I+calcium chlorate, compound offormula I+cafenstrole, compound of formula I+carbetamide, compound offormula I+carfentrazone, compound of formula I+carfentrazone-ethyl,compound of formula I+CDEA, compound of formula I+CEPC, compound offormula I+chlorflurenol, compound of formula I+chlorflurenol-methyl,compound of formula I+chloridazon, compound of formula I+chlorimuron,compound of formula I+chlorimuron-ethyl, compound of formulaI+chloroacetic acid, compound of formula I+chlorotoluron, compound offormula I+chlorpropham, compound of formula I+chlorsulfuron, compound offormula I+chlorthal, compound of formula I+chlorthal-dimethyl, compoundof formula I+cinidon-ethyl, compound of formula I+cinmethylin, compoundof formula I+cinosulfuron, compound of formula I+cisanilide, compound offormula I+clethodim, compound of formula I+clodinafop, compound offormula I+clodinafop-propargyl, compound of formula I+clomazone,compound of formula I+clomeprop, compound of formula I+clopyralid,compound of formula I+cloransulam, compound of formulaI+cloransulam-methyl, compound of formula I+CMA, compound of formulaI+4-CPB, compound of formula I+CPMF, compound of formula I+4-CPP,compound of formula I+CPPC, compound of formula I+cresol, compound offormula I+cumyluron, compound of formula I+cyanamide, compound offormula I+cyanazine, compound of formula I+cycloate, compound of formulaI+cyclosulfamuron, compound of formula I+cycloxydim, compound of formulaI+cyhalofop, compound of formula I+cyhalofop-butyl, compound of formulaI+2,4-D, compound of formula I+3,4-DA, compound of formula I+daimuron,compound of formula I+dalapon, compound of formula I+dazomet, compoundof formula I+2,4-DB, compound of formula I+3,4-DB, compound of formulaI+2,4-DEB, compound of formula I+desmedipham, compound of formulaI+dicamba, compound of formula I+dichlobenil, compound of formulaI+ortho-dichlorobenzene, compound of formula I+para-dichlorobenzene,compound of formula I+dichlorprop, compound of formula I+dichlorprop-P,compound of formula I+diclofop, compound of formula I+diclofop-methyl,compound of formula I+diclosulam, compound of formula I+difenzoquat,compound of formula I+difenzoquat metilsulfate, compound of formulaI+diflufenican, compound of formula I+diflufenzopyr, compound of formulaI+dimefuron, compound of formula I+dimepiperate, compound of formulaI+dimethachlor, compound of formula I+dimethametryn, compound of formulaI+dimethenamid, compound of formula I+dimethenamid-P, compound offormula I+dimethipin, compound of formula I+dimethylarsinic acid,compound of formula I+dinitramine, compound of formula I+dinoterb,compound of formula I+diphenamid, compound of formula I+diquat, compoundof formula I+diquat dibromide, compound of formula I+dithiopyr, compoundof formula I+diuron, compound of formula I+DNOC, compound of formulaI+3,4-DP, compound of formula I+DSMA, compound of formula I+EBEP,compound of formula I+endothal, compound of formula I+EPTC, compound offormula I+esprocarb, compound of formula I+ethalfluralin, compound offormula I+ethametsulfuron, compound of formula I+ethametsulfuron-methyl,compound of formula I+ethofumesate, compound of formula I+ethoxyfen,compound of formula I+ethoxysulfuron, compound of formula I+etobenzanid,compound of formula I+fenoxaprop-P, compound of formulaI+fenoxaprop-P-ethyl, compound of formula I+fentrazamide, compound offormula I+ferrous sulfate, compound of formula I+flamprop-M, compound offormula I+flazasulfuron, compound of formula I+florasulam, compound offormula I+fluazifop, compound of formula I+fluazifop-butyl, compound offormula I+fluazifop-P, compound of formula I+fluazifop-P-butyl, compoundof formula I+flucarbazone, compound of formula I+flucarbazone-sodium,compound of formula I+flucetosulfuron, compound of formulaI+fluchloralin, compound of formula I+flufenacet, compound of formulaI+flufenpyr, compound of formula I+flufenpyr-ethyl, compound of formulaI+flumetsulam, compound of formula I+flumiclorac, compound of formulaI+flumiclorac-pentyl, compound of formula I+flumioxazin, compound offormula I+fluometuron, compound of formula I+fluoroglycofen, compound offormula I+fluoroglycofen-ethyl, compound of formula I+flupropanate;compound of formula I+flupyrsulfuron, compound of formulaI+flupyrsulfuron-methyl-sodium, compound of formula I+flurenol, compoundof formula I+fluridone, compound of formula I+fluorochloridone, compoundof formula I+fluoroxypyr, compound of formula I+flurtamone, compound offormula I+fluthiacet, compound of formula I+fluthiacet-methyl, compoundof formula I+fomesafen, compound of formula I+foramsulfuron, compound offormula I+fosamine, compound of formula I+glufosinate, compound offormula I+glufosinate-ammonium, compound of formula I+glyphosate,compound of formula I+halosulfuron, compound of formulaI+halosulfuron-methyl, compound of formula I+haloxyfop, compound offormula I+haloxyfop-P, compound of formula I+HC-252, compound of formulaI+hexazinone, compound of formula I+imazamethabenz, compound of formulaI+imazamethabenz-methyl, compound of formula I+imazamox, compound offormula I+imazapic, compound of formula I+imazapyr, compound of formulaI+imazaquin, compound of formula I+imazethapyr, compound of formulaI+imazosulfuron, compound of formula I+indanofan, compound of formulaI+iodomethane, compound of formula I+iodosulfuron, compound of formulaI+iodosulfuron-methyl-sodium, compound of formula I+ioxynil, compound offormula I+isoproturon, compound of formula I+isouron, compound offormula I+isoxaben, compound of formula I+isoxachlortole, compound offormula I+isoxaflutole, compound of formula I+karbutilate, compound offormula I+lactofen, compound of formula I+lenacil, compound of formulaI+linuron, compound of formula I+MAA, compound of formula I+MAMA,compound of formula I+MCPA, compound of formula I+MCPA-thioethyl,compound of formula I+MCPB, compound of formula I+mecoprop, compound offormula I+mecoprop-P, compound of formula I+mefenacet, compound offormula I+mefluidide, compound of formula I+mesosulfuron, compound offormula I+mesosulfuron-methyl, compound of formula I+mesotrione,compound of formula I+metam, compound of formula I+metamifop, compoundof formula I+metamitron, compound of formula I+metazachlor, compound offormula I+methabenzthiazuron, compound of formula I+methylarsonic acid,compound of formula I+methyldymron, compound of formula I+methylisothiocyanate, compound of formula I+metobenzuron, compound of formulaI+metolachlor, compound of formula I+S-metolachlor, compound of formulaI+metosulam, compound of formula I+metoxuron, compound of formulaI+metribuzin, compound of formula I+metsulfuron, compound of formulaI+metsulfuron-methyl, compound of formula I+MK-616, compound of formulaI+molinate, compound of formula I+monolinuron, compound of formulaI+MSMA, compound of formula I+naproanilide, compound of formulaI+napropamide, compound of formula I+naptalam, compound of formulaI+neburon, compound of formula I+nicosulfuron, compound of formulaI+nonanoic acid, compound of formula I+norflurazon, compound of formulaI+oleic acid (fatty acids), compound of formula I+orbencarb, compound offormula I+orthosulfamuron, compound of formula I+oryzalin, compound offormula I+oxadiargyl, compound of formula I+oxadiazon, compound offormula I+oxasulfuron, compound of formula I+oxaziclomefone, compound offormula I+oxyfluorfen, compound of formula I+paraquat, compound offormula I+paraquat dichloride, compound of formula I+pebulate, compoundof formula I+pendimethalin, compound of formula I+penoxsulam, compoundof formula I+pentachlorophenol, compound of formula I+pentanochlor,compound of formula I+pentoxazone, compound of formula I+pethoxamid,compound of formula I+petrolium oils, compound of formulaI+phenmedipham, compound of formula I+phenmedipham-ethyl, compound offormula I+picloram, compound of formula I+picolinafen, compound offormula I+pinoxaden, compound of formula I+piperophos, compound offormula I+potassium arsenite, compound of formula I+potassium azide,compound of formula I+pretilachlor, compound of formula I+primisulfuron,compound of formula I+primisulfuron-methyl, compound of formulaI+prodiamine, compound of formula I+profluazol, compound of formulaI+profoxydim, compound of formula I+prometon, compound of formulaI+prometryn, compound of formula I+propachlor, compound of formulaI+propanil, compound of formula I+propaquizafop, compound of formulaI+propazine, compound of formula I+propham, compound of formulaI+propisochlor, compound of formula I+propoxycarbazone, compound offormula I+propoxycarbazone-sodium, compound of formula I+propyzamide,compound of formula I+prosulfocarb, compound of formula I+prosulfuron,compound of formula I+pyraclonil, compound of formula I+pyraflufen,compound of formula I+pyraflufen-ethyl, compound of formulaI+pyrazolynate, compound of formula I+pyrazosulfuron, compound offormula I+pyrazosulfuron-ethyl, compound of formula I+pyrazoxyfen,compound of formula I+pyribenzoxim, compound of formula I+pyributicarb,compound of formula I+pyridafol, compound of formula I+pyridate,compound of formula I+pyriftalid, compound of formula I+pyriminobac,compound of formula I+pyriminobac-methyl, compound of formulaI+pyrimisulfan, compound of formula I+pyrithiobac, compound of formulaI+pyrithiobac-sodium, compound of formula I+quinclorac, compound offormula I+quinmerac, compound of formula I+quinoclamine, compound offormula I+quizalofop, compound of formula I+quizalofop-P, compound offormula I+rimsulfuron, compound of formula I+sethoxydim, compound offormula I+siduron, compound of formula I+simazine, compound of formulaI+simetryn, compound of formula I+SMA, compound of formula I+sodiumarsenite, compound of formula I+sodium azide, compound of formulaI+sodium chlorate, compound of formula I+sulcotrione, compound offormula I+sulfentrazone, compound of formula I+sulfometuron, compound offormula I+sulfometuron-methyl, compound of formula I+sulfosulfaron,compound of formula I+sulfuric acid, compound of formula I+tar oils,compound of formula I+2,3,6-TBA, compound of formula I+TCA, compound offormula I+TCA-sodium, compound of formula I+tebuthiuron, compound offormula I+tepraloxydim, compound of formula I+terbacil, compound offormula I+terbumeton, compound of formula I+terbuthylazine, compound offormula I+terbutryn, compound of formula I+thenylchlor, compound offormula I+thiazopyr, compound of formula I+thifensulfuron, compound offormula I+thifensulfuron-methyl, compound of formula I+thiobencarb,compound of formula I+tiocarbazil, compound of formula I+topramezone,compound of formula I+tralkoxydim, compound of formula I+tri-allate,compound of formula I+triasulfuron, compound of formula I+triaziflam,compound of formula I+tribenuron, compound of formulaI+tribenuron-methyl, compound of formula I+tricamba, compound of formulaI+triclopyr, compound of formula I+trietazine, compound of formulaI+trifloxysulfuron, compound of formula I+trifloxysulfuron-sodium,compound of formula I+trifluralin, compound of formula I+triflusulfuron,compound of formula I+triflusulfuron-methyl, compound of formulaI+trihydroxytriazine, compound of formula I+tritosulfuron, compound offormulaI+[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]aceticacid ethyl ester.

The mixing partners of the compound of formula I may also be in the formof esters or salts, as mentioned e.g. in The Pesticide Manual, 12thEdition (BCPC), 2000.

The mixing ratio of the compound of formula I to the mixing partner ispreferably from 1:100 to 1000:1.

The mixtures can advantageously be used in the above-mentionedformulations (in which case “active ingredient” relates to therespective mixture of compound of formula I with the mixing partner).

Preferred mixtures of a compound of formula I with one or more furtherherbicides include:

Mixtures of a compound of the formula I with a triazine (e.g. compoundof formula I+ametryn, compound of formula I+atrazine, compound offormula I+cyanazine, compound of formula I+dimethametryn, compound offormula I+metribuzin, compound of formula I+prometon, compound offormula I+prometryn, compound of formula I+propazine, compound offormula I+simazine, compound of formula I+simetryn, compound of formulaI+terbumeton, compound of formula I+terbuthylazine, compound of formulaI+terbutryn, compound of formula I+trietazine). Particularly preferredare mixtures of a compound of formula I with atrazine, metribuzin,prometryn or with terbuthylazine (i.e. compound of formula I+atrazine,compound of formula I+metribuzin, compound of formula I+prometryn, andcompound of formula I+terbuthylazine).

Mixtures of a compound of formula I with isoxaflutole.

Mixtures of a compound of formula I with isoxaflutole and a triazine.

Mixtures of a compound of formula I with isoxaflutole and glyphosate.

Mixtures of a compound of formula I with isoxaflutole and glufosinate.

Mixtures of a compound of formula I with mesotrione.

Mixtures of a compound of formula I with mesotrione and a triazine.

Mixtures of a compound of formula I with mesotrione and glyphosate.

Mixtures of a compound of formula I with mesotrione and glufosinate.

Mixtures of a compound of formula I with sulcotrione.

Mixtures of a compound of formula I with sulcotrione and a triazine.

Mixtures of a compound of formula I with sulcotrione and glyphosate.

Mixtures of a compound of formula I with sulcotrione and glufosinate.

Mixtures of a compound of formula I with a triazolinone (e.g. compoundof formula I+amicarbazone).

Mixtures of a compound of formula I with an ALS inhibitor (e.g. compoundof formula I+chlorsulfuron, compound of formula I+cinosulfuron, compoundof formula I+cloransulam, compound of formula I+ethametsulfuron,compound of formula I+flazasulfuron, compound of formulaI+foramsulfuron, compound of formula I+flumetsulam, compound of formulaI+imazamethabenz, compound of formula I+imazamox, compound of formulaI+imazapic, compound of formula I+imazapyr, compound of formulaI+imazethapyr, compound of formula I+iodosulfuron, compound of formulaI+metsulfuron, compound of formula I+nicosulfuron, compound of formulaI+oxasulfuron, compound of formula I+primisulfuron, compound of formulaI+prosulfuron, compound of formula I+pyrithiobac, compound of formulaI+rimsulfuron, compound of formula I+sulfosulfuron, compound of formulaI+thifensulfuron, compound of formula I+triasulfuron, compound offormula I+tribenuron, compound of formula I+trifloxysulfuron, compoundof formulaI+4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo)-1H-1,2,4-triazol-1-ylcarbonylsulfamoyl]-5-methylthiophene-3-carboxylicacid (BAY636)). Particularly preferred are mixtures of a compound offormula I with flazasulfuron, foramsulfuron, flumetsulam, imazapyr,imazethapyr, iodosulfuron, nicosulfuron, rimsulfuron, trifloxysulfuronor with4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo)-1H-1,2,4-triazol-1-ylcarbonylsulfamoyl]-5-methylthiophene-3-carboxylicacid (BAY636) (i.e. compound of formula I+flazasulfuron, compound offormula I+foramsulfuron, compound of formula I+flumetsulam, compound offormula I+imazapyr, compound of formula I+imazethapyr, compound offormula I+iodosulfuron, compound of formula I+nicosulfuron, compound offormula I+rimsulfuron, compound of formula I+trifloxysulfuron, andcompound of formulaI+4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo)-1H-1,2,4-triazol-1-ylcarbonylsulfamoyl]-5-methylthiophene-3-carboxylicacid (BAY636)).

Mixtures of a compound of formula I with a PPO inhibitor (e.g. compoundof formula I+fomesafen, compound of formula I+flumioxazin, compound offormula I+sulfentrazone, compound of formulaI+[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoro-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]aceticacid ethyl ester). Particularly preferred are mixtures of a compound offormula I with flumioxazin, sulfentrazone or[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]aceticacid ethyl ester (i.e. compound of formula I+flumioxazin, compound offormula I+sulfentrazone, and compound of formulaI+[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]aceticacid ethyl ester).

Mixtures of a compound of formula I with glyphosate.

Mixtures of a compound of formula I with glufosinate.

Mixtures of a compound of formula I with paraquat.

Mixtures of a compound of formula I with pendimethalin or a compound offormula I with trifluralin. Particularly preferred are mixtures of acompound of formula I with pendimethalin.

Mixtures of a compound of formula I with metamitron.

Mixtures of a compound of formula I with clomazone.

Mixtures of a compound of formula I with metazachlor.

Mixtures of a compound of formula I with clodinafop or a compound offormula I with pinoxaden.

The compounds of formula I according to the invention can also be usedin combination with safeners. Likewise, mixtures of a compound offormula I according to the invention with one or more further herbicidescan also be used in combination with one or more safeners. The safenerscan be cloquintocet-mexyl (CAS RN 99607-70-2) or a lithium, sodium,potassium, calcium, magnesium, aluminium, iron, ammonium, quaternaryammonium, sulfonium or phosphonium salt thereof such as those disclosedin WO 02/34048, fenchlorazol-ethyl (CAS RN 103112-35-2) and thecorresponding acid (CAS RN 103112-36-3), mefenpyr-diethyl (CAS RN135590-91-9) and the corresponding di-acid (CAS RN 135591-00-3),isoxadifen-ethyl (CAS RN 163520-33-0) and the corresponding acid (CAS RN209866-92-2), furilazole (CAS RN 121776-33-8) and the corresponding Risomer (CAS RN 121776-57-6), benoxacor (CAS RN 98730-04-2), dichlormid(CAS RN 37764-25-3), MON4660 (CAS RN 71526-07-3), oxabetrinil (CAS RN74782-23-3), cyometrinil (CAS RN 78370-21-5) and the corresponding (Z)isomer (CAS RN 63278-33-1), fenclorim (CAS RN 3740-92-9),N-cyclopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (CAS RN221667-31-8), N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (CASRN 221668-34-4), naphthalic anhydride (CAS RN 81-84-5) and flurazole(CAS RN 72850-64-7).

Preferably the mixing ratio of compound of formula I to safener is from100:1 to 1:10, especially from 20:1 to 1:1.

The mixtures can advantageously be used in the above-mentionedformulations (in which case “active ingredient” relates to therespective mixture of compound of formula I with the safener).

Preferred mixtures of a compound of formula I with further herbicidesand safeners include:

Mixtures of a compound of formula I with a triazine and a safener.

Mixtures of a compound of formula I with glyphosate and a safener.

Mixtures of a compound of formula I with glufosinate and a safener.

Mixtures of a compound of formula I with isoxaflutole and a safener.

Mixtures of a compound of formula I with isoxaflutole and a triazine anda safener.

Mixtures of a compound of formula I with isoxaflutole and glyphosate anda safener.

Mixtures of a compound of formula I with isoxaflutole and glufosinateand a safener.

Mixtures of a compound of formula I with mesotrione and a safener.

Mixtures of a compound of formula I with mesotrione and a triazine and asafener.

Mixtures of a compound of formula I with mesotrione and glyphosate and asafener.

Mixtures of a compound of formula I with mesotrione and glufosinate anda safener.

Mixtures of a compound of formula I with sulcotrione and a safener.

Mixtures of a compound of formula I with sulcotrione and a triazine anda safener.

Mixtures of a compound of formula I with sulcotrione and glyphosate anda safener.

Mixtures of a compound of formula I with sulcotrione and glufosinate anda safener.

The following Examples further illustrate, but do not limit, theinvention.

PREPARATION EXAMPLES Example P1 Preparation of3-{2,6-difluoro-phenylmethane(N-trifluoromethyl-carbonyl)sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

Trifluoroacetamide (356 mg, 3.15 mmol), magnesium oxide (254 mg, 6.3mmol), rhodium(II) acetate dimer (17.4 mg, 0.04 mmol) and iodobenzenediacetate (761 mg, 2.36 mmol) was added to a solution of3-(2,6-difluoro-phenylmethanesulfinyl)-5,5-dimethyl-4,5-dihydroisoxazole(430 mg, 1.58 mmol) in dichloromethane (16 ml) under nitrogen and thedark green solution was stirred for 12 hours at room temperature. Themixture was filtered through celite, the celite was washed withdichloromethane and the filtrate was concentrated. The crude product waspurified by chromatography on silica gel (eluent: hexane/ethyl acetate)to give the product (Compound No. 1.04 of Table 65) as yellow solid (282mg, 47% yield).

The following compounds were synthesised as described in Example P1:

Compound No. 1.11 of Table 65 using 4-nitrophenylsulfonamide as reagent,

Compound No. 1.12 of Table 65 using methylsulfonamide as reagent,

Compound No. 1.06 of Table 65 using carbamic acid tert.-butylester asreagent

Compound No. 2.02 of Table 66 using3-(5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfinyl)-5,5-dimethyl-4,5-dihydroisoxazoleas starting material,

Compound No. 2.05 of Table 66 using3-(1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfinyl)-5,5-dimethyl-4,5-dihydroisoxazole,and

Compound No. 2.08 of Table 66 using3-(3-difluoromethyl-1-methyl-1H-pyrazol-4-yl-methanesulfinyl)-5,5-dimethyl-4,5-dihydroisoxazole.

Example P2 Preparation of3-{2,6-difluoro-phenylmethane-sulfoximinyl-5,5-dimethyl-4,5-dihydroisoxazole

Potassium carbonate (77 mg, 0.56 mmol) was added to3-{2,6-difluoro-phenyl-methane(N-trifluoromethylcarbonyl)-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

(Compound No. 1.04 of Table 65) (194 mg, 0.51 mmol) in methanol (0.2ml). After 15 minutes the mixture was concentrated and partitionedbetween dichloromethane and water. The organic phase was washed withbrine, dried over magnesium sulfate and concentrated to give a paleyellow gum that solidified upon standing to give the product (Compound1.01 of Table 65) as cream solid (133 mg, 98% yield).

The following compounds were synthesised as described in Example P2:

Compound No. 1.02 of Table 65 from Compound No. 1.05 of Table 65,

Compound No. 1.22 of Table 65 from Compound No. 1.38 of Table 65,

Compound No. 1.52 of Table 65 from Compound No. 1.50 of Table 65,

Compound No. 1.53 of Table 65 from Compound No. 1.51 of Table 65,

Compound No. 2.01 of Table 66 from Compound No. 2.02 of Table 66,

Compound No. 2.06 of Table 66 from Compound No. 2.05 of Table 66, and

Compound No. 2.07 of Table 66 from Compound No. 2.08 of Table 66.

The following compound was synthesised as described in Example P11followed by the procedure described in Example P2:

Compound No. 1.56 of Table 65 from3-{3-trifluoromethoxy-phenylmethane(N-[4-nitrobenzoyl])-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole.

The following compound was synthesised as described in Example P12followed by the procedure described in Example P2:

Compound No. 1.57 of Table 65 from3-{3-trifluoromethoxy-phenylmethane(N-[4-nitrobenzoyl])-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole.

Compound No. 2.03 of Table 66 from3-{5-methoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethane(N-[4-nitrobenzoyl])-sulfoximinyl)-5,5-dimethyl-4,5-dihydro-isoxazole.

The following compound was synthesised as described in Example P1followed by the procedure described in Example P2: Compound No. 2.04 ofTable 66 from3-(3-difluoromethoxy-1-methyl-5-trifluoromethyl-1H-pyrazol-4-ylmethanesulfinyl)-5,5-dimethyl-4,5-dihydro-isoxazole.

Example P3 Preparation of3-{2,6-difluoro-phenylmethane(N-methyl)sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

A solution of3-{2,6-difluoro-phenylmethanesulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.01 of Table 65) (50 mg, 0.17 mmol) in dichloro-methane(0.2 ml) was added dropwise to a suspension of trimethyloxoniumtetrafluoro-borate (26 mg, 0.17 mmol) in dichloromethane (0.5 ml) undernitrogen. After 12 hours at room temperature, the mixture was washedwith sodium bicarbonate, the aqueous phase was extracted several timeswith dichloromethane. The combined organic phases were dried overmagnesium sulfate and concentrated. The crude product was purified bychromatography on silica gel (eluent: hexane/ethyl acetate) to give theproduct (Compound 1.08 of Table 65) as a white solid (15 mg, 29% yield).

Example P4 Preparation of3-{2,6-difluoro-phenylmethane(N-[4-chlorobenzoyl]-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

Triethylamine (0.76 ml, 5.5 mmol) and 4-chlorobenzoyl chloride (0.53 ml,5.2 mmol) were added dropwise to3-{2,6-difluoro-phenylmethanesulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.01 of Table 65) (1.2 g, 4.2 mmol) in dichloromethane (10ml) at 0° C. under nitrogen. The mixture was stirred for 1 hour at 0° C.and for 10 hours at room temperature, poured into water and extractedseveral times with dichloromethane. The combined organic phases weredried over magnesium sulfate, concentrated and purified bychromatography on silica gel (eluent: hexane/ethyl acetate) to give theproduct (Compound No. 1.03 of Table 65) as a white solid (540 mg, 53%yield).

The following compounds were synthesised as described in Example P4:

Compound No. 1.07 of Table 65 using acetyl chloride as reagent,

Compound No. 1.17 of Table 65 using 1-chloroethyl chloroformate asreagent,

Compound No. 1.21 of Table 65 using 2-chloronicotinoyl chloride asreagent,

Compound No. 1.36 of Table 65 using benzoyl chloride as reagent, and

Compound No. 1.45 of Table 65 using 4-nitrobenzoyl chloride as reagent.

Example P5 Preparation of3-{2,6-difluoro-phenylmethane(N-[trimethylsilyl]-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

N,N-Diethyltrimethylsilylamine (0.07 ml, 0.39 mmol) was added dropwiseto a solution of3-{2,6-difluoro-phenylmethanesulfoximinyl)-5,5-dimethyl-4,5-dihydro-isoxazole(Compound No. 1.01 of Table 65) (100 mg, 0.35 mmol) in acetonitrile (2ml) at 65° C. under nitrogen. After stirring for 1.5 hours at 65° C. andfor 10 hours at room temperature the mixture was concentrated to givethe product (Compound No. 1.10 of Table 65) as a pale orange gum (117mg, purity 80%).

Example P6 Preparation of3-{2,6-difluoro-phenyl-chloromethane(N-[trifluoroacetyl]-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

1-tert-Butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catena-di(phosphazene)(P₂-^(t)Bu) (2M in THF) (0.14 ml, 0.29 mmol) was added to a solution of3-{2,6-difluoro-phenylmethane(N-trifluoromethylcarbonyl)sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.04 of Table 65) (100 mg, 0.26 mmol) in THF (3 ml) undernitrogen. After 10 minutes N-chlorosuccinimide (NCS) (38 mg, 0.29 mmol)was added and the mixture stirred for 10 minutes. The mixture was pouredinto aqueous hydrochloric acid (1M) and extracted several times withethyl acetate. The combined organic phases were dried over magnesiumsulfate, concentrated and purified by chromatography on silica gel(eluent: hexane/ethyl acetate) to give the product (Compound No. 1.05 ofTable 65) as a white solid (50 mg, 46% yield).

Example P7 Preparation of3-{2,6-difluoro-phenyl-methane(N-[formyl]sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

3-{2,6-Difluoro-phenylmethanesulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.01 of Table 65) (100 mg, 0.35 mmol) and a catalyticamount of p-toluenesulfonic acid was dissolved in trimethyl orthoformate(1 ml) and heated to 90° C. for 3.5 hours. The mixture was cooled toroom temperature, concentrated and the crude product was purified bychromatography on silica gel (eluent: hexane/ethyl acetate) to give theproduct (Compound No. 1.13 of Table 65) (8 mg, 11% yield).

Example P8 Preparation of3-{2,6-difluoro-phenyl-methane(N-[nitro]sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

3-{2,6-Difluoro-phenylmethanesulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.01 of Table 65) (100 mg, 0.35 mmol) was dissolved indichloro-methane (0.7 ml) and fuming nitric acid (15 μl, 0.35 mmol) wasadded. After 10 minutes the mixture was cooled to 0° C. and aceticanhydride (0.7 ml, 7.29 mmol) and 1 drop of concentrated sulfuric acidwere added. The mixture was stirred for 20 minutes at 0° C. and for 1.5hours at room temperature, was diluted with ethyl acetate and washedseveral times with water and saturated aqueous sodium bicarbonatesolution. The aqueous phase was extracted with ethyl acetate, thecombined organic phases were washed again with water, dried overmagnesium sulfate and concentrated. Trituration with n-hexane furnishedthe product (Compound No. 1:15 of Table 65) (54.8 mg, 47% yield).

Example P9 Preparation of3-{2,6-difluoro-phenyl-methane(N-[trifluoroacetyl]-sulfiliminyl)-5,5-dimethyl-4,5-dihydroisoxazole

Trifluoroacetamide (4.4 g, 38.9 mmol), magnesium oxide (3.1 g, 77.7mmol), rhodium(II) acetate dimer (217 mg, 0.49 mmol) and iodobenzenediacetate (9.4 g, 29.1 mmol) were added to a solution of3-(2,6-difluoro-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole(5 g, 19.4 mmol) in dichloromethane (150 ml) under nitrogen and the greysuspension was stirred for 12 hours at room temperature. The mixture wasfiltered and the filtrate was concentrated. The crude product waspurified by chromatography on silica gel (eluent: hexane/ethyl acetate)to give the product (Compound No. 1.09 of Table 65) (6.7 g, 90% purity,84% yield).

Example P10 Preparation of3-{2,6-difluoro-phenylmethane-sulfoximinyl-5,5-dimethyl-4,5-dihydroisoxazole

Potassium carbonate (5.3 g, 38.4 mmol) in water (13 ml) was added to asolution of3-{2,6-difluoro-phenylmethane(N-trifluoromethylcarbonyl)sulfilimyl)-5,5-dimethyl-4,5-dihydrisoxazole(Compound No. 1.09 of Table 65) (6.7 g, 18.3 mmol) in ethanol (90 ml). Asolution of m-chloroperoxybenzoic acid (50-70% weight) (8.84 g, 30.7mmol) in ethanol (30 ml) was added dropwise and the mixture stirred for1 hour at room temperature. The reaction was quenched by addition of 40%aqueous metabisulfite solution (50 ml). The mixture was stirred for 10minutes before it was extracted several times with ethyl acetate. Thecombined organic phases were washed with saturated aqueous sodiumbicarbonate and brine, dried over magnesium sulfate and concentrated togive the product (Compound No. 1.01 of Table 65) as a white solid (3.7g, 70% yield).

The following compounds were synthesised as described in Example P9followed by the procedure described in Example P10:

Compound No. 1.24 of Table 65 from3-(2-trifluoromethoxy-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,Compound No. 1.25 of Table 65 from3-(2-difluoromethoxy-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,

Compound No. 1.26 of Table 65 from3-(2-trifluoromethylthio-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,Compound No. 1.27 of Table 65 from3-(2-tolyl-methanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole, CompoundNo. 1.28 of Table 65 from3-(2,6-difluoro-3-tolylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,

Compound No. 1.29 of Table 65 from3-(2,3-difluoro-phenylmethanesulfanyl)-5,5-di-methyl-4,5-dihydroisoxazole,Compound No. 1.30 of Table 65 from3-(2,4-difluoro-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,Compound No. 1.31 of Table 65 from3-(2-trifluoromethyl-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydro-isoxazole,Compound No. 1.32 of Table 65 from3-(2-fluoro-6-trifluoromethylphenyl-methanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,Compound No. 1.33 of Table 65 from3-(2-biphenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,

Compound No. 1.34 of Table 65 from3-(2,5-difluoro-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,Compound No. 1.39 of Table 65 from3-(2-fluoro-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,Compound No. 1.40 of Table 65 from3-(3,5-difluoro-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydro-isoxazole,Compound No. 1.41 of Table 65 from3-(2-cyano-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,Compound No. 1.42 of Table 65 from3-phenyl-methanesulfanyl-5,5-dimethyl-4,5-dihydroisoxazole, Compound No.1.46 of Table 65 from3-(2-fluoro-4-methoxycarbonyl-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydro-isoxazole,Compound No. 1.47 of Table 65 from3-(4-ethoxycarbonyl-2-fluoro-phenyl-methanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole,Compound No. 1.48 of Table 65 from 3-(6-fluoro-4H-benzo[1,3]dioxin-8-ylmethanesulfanyl)-5,5-dimethyl-4,5-dihydro-isoxazole, Compound No. 1.49of Table 65 was isolated during the synthesis of Compound No. 1.48 ofTable 65, Compound No. 1.59 of Table 65 from3-(2-chloro-3-ethoxycarbonyl-6-methylsulfonyl-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole.

Example P11 Preparation of3-{2,6-difluoro-phenylfluoromethane(N-[4-nitrobenzoyl]-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

To a solution of3-{2,6-difluoro-phenylmethane(N-[4-nitrobenzoyl]sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.45 of Table 65) (500 mg, 1.14 mmol) in THF (5 ml) wasadded N′-tert-butyl-N,N,N′,N′,N″,N″-hexamethyl-phosphorimidic triamide(P₁-^(t)Bu) (0.31 ml, 1.2 mmol) dropwise. After 10 minutesN-fluorobenzenesulfonimide (NFSI) (378 mg, 2.58 mmol) was added and themixture stirred for 5 hours. The mixture was concentrated and purifiedby chromatography on silica gel (eluent: hexane/ethyl acetate) to givediastereomer A (Compound No. 1.50 of Table 65) as a white solid (340 mg,65% yield) and diastereomer B (Compound No. 1.51 of Table 65) as a whitesolid (103 mg, 20% yield).

The following compounds were synthesised as described in Example P11:

Compound No. 1.35 of Table 65 from Compound No. 1.36 of Table 65, and

Compound No. 1.43 of Table 65 from Compound No. 1.03 of Table 65.

Example P12 Preparation of3-{2,6-difluoro-phenyldifluoromethane(N-[benzoyl]-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

To a solution of3-{2,6-difluoro-phenylmethane(N-[benzoyl]sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.36 of Table 65) (155 mg, 0.39 mmol) in THF (5 ml) wasadded1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-^(t)Bu) (2M in THF) (0.44 ml, 0.87 mmol) dropwise. After 10 minutesN-fluorobenzenesulfonimide (NFSI) (274 mg, 0.87 mmol) was added and themixture stirred for 30 minutes. The mixture was concentrated andpurified by chromatography on silica gel (eluent: hexane/ethyl acetate)to give the product (Compound No. 1.37 of Table 65) as a white solid (94mg, 56% yield).

Compound No. 1.38 of Table 65 was were synthesised as described inExample P12 from Compound No. 1.45 of Table 65.

Example P13 Preparation of3-{2,6-difluoro-phenyldifluoromethane(N-[4-chloro-benzoyl]sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

To a solution of3-{2,6-difluoro-phenylfluoromethane(N-[4-chlorobenzoyl]-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.43 of Table 65) (450 mg, 1.0 mmol) in THF (5 ml) wasadded1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-^(t)Bu) (2M in THF) (0.55 ml, 1.1 mmol) dropwise. After 10 minutesN-fluorobenzenesulfonimide (NFSI) (350 mg, 1.1 mmol) was added and themixture stirred for 30 minutes. The mixture was concentrated andpurified by chromatography on silica gel (eluent: hexane/ethyl acetate)to give the product (Compound No. 1.44 of Table 65) as a white solid(200 mg, 53% yield).

Example P14 Preparation of3-{2,6-difluoro-phenylfluorochloromethanesulfoximinyl-5,5-dimethyl-4,5-dihydroisoxazole

A diastereomeric mixture of3-{2,6-difluoro-phenylfluoromethane(N-[4-nitrobenzoyl]sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.50 of Table 65 and Compound No. 1.51 of Table 65) (300mg, 0.66 mmol) and hexachloroethane (172 mg, 0.72 mmol) were dissolvedin THF (5 ml) and1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-Et) (0.24 ml, 0.72 mmol) was added dropwise at 0° C. After 30minutes several drops of saturated aqueous ammonium chloride solutionwas added and the mixture was concentrated. The residue was dissolved inmethanol (5 ml) and potassium carbonate (100 mg, 0.72 mmol) was added.After 2 hours the mixture was concentrated, the residue dissolved indichloromethane, washed several times with saturated aqueous sodiumbicarbonate solution, and brine, and dried over magnesium sulfate. Themixture was concentrated and purified by chromatography on silica gel(eluent: hexane/ethyl acetate) to give diastereomer A (Compound No. 1.54of Table 65) as a white solid (27 mg, 12% yield) and diastereomer B(Compound No. 1.55 of Table 65) as a white solid (57 mg, 25% yield).

Example P15 Preparation of3-{1′-[2,6-difluoro-phenyl]ethane(N-[trifluoroacetyl]-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

To a solution of3-{2,6-difluoro-phenylmethane(N-trifluoromethyl-carbonyl)sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.04 of Table 65) (227 mg, 0.59 mmol) in THF (10 m) wasadded1-tert-butyl-2,2,4,4,4-pentakis-(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-^(t)Bu) (2M in THF) (0.3 ml, 0.65 mmol) under nitrogen at roomtemperature. After 5 minutes dimethyl sulfate (109 μL, 0.65 mmol) wasadded and the mixture stirred for 30 minutes. The reaction was quenchedby addition of aqueous hydrochloric acid (2M) (0.5 ml) and extractedwith ethyl acetate. The combined organic extracts were washed withbrine, dried over magnesium sulfate, filtered through silica gel andconcentrated. The residue was purified by preparative HPLC (20% ethylacetate/hexane) to give diastereomer A (Compound No. 1.19 of Table 65)as a colourless gum (58 mg, 25% yield) and diastereomer B (Compound No.1.20 of Table 65) as a colourless gum (45 mg, 19% yield).

Example P16 Preparation of3-{2,6-difluoro-phenylmethane(N-trifluoromethylsulphonyl)-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

3-{2,6-difluoro-phenylmethanesulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.01 of Table 65) (100 mg, 0.35 mmol) and pyridine (0.08ml, 1.04 mmol) were dissolved in dichloromethane (5 ml) andtrifluoromethanesulfonic anhydride (0.09 ml, 0.52 mmol) was addeddropwise at 0° C. The mixture was allowed to warm to room temperatureand stirred for 4 h. The mixture was diluted with ethyl acetate (10 ml),washed with water (10 ml) and 2M HCl (10 ml), dried over MgSO4 andconcentrated. Purification by chromatography on silica gel (eluent:hexane/ethyl acetate) gave the product (Compound No. 1.14 of Table 65)as a colourless gum (78 mg, 53% yield).

Example P17 Preparation of3-{2,6-difluoro-phenylmethane(N-[4-trifluoromethyl-2-pyrimidyl])-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

3-{2,6-difluoro-phenylmethanesulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.01 of Table 65) (200 mg, 0.69 mmol) was dissolved intetrahydrofuran (3 ml) and1-tert-Butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda⁵-5,4-lambda⁵-5-catenadi(phosphazene)(P₂-^(t)Bu) (2M in THF) (0.42 ml, 0.83 mmol) was added dropwise,followed by 2-chloro-4-trifluoromethylpyrimidine (152 mg, 0.83 mmol).The mixture was stirred at room temperature for 24 h, then was heated toreflux for 5 h. After cooling, ethyl acetate (10 ml) was added and themixture was washed with 2M HCl (10 ml), dried over MgSO₄ andconcentrated. Purification by chromatography on silica gel (eluent:hexane/ethyl acetate) gave the product (Compound No. 1.16 of Table 65)as a white solid (83 mg, 28% yield).Compound No. 1.23 of Table 65 was synthesised as described in ExampleP17 using 4-chloro-5-cyanopyrimidine as reagent,

Example P18 Preparation of3-{2,6-difluoro-phenyl-methane(N-4-nitrophenylsulphonyl]sulfiliminyl)-5,5-dimethyl-4,5-dihydroisoxazole

4-Nitrobenzenesulphonamide (189 mg, 0.93 mmol), silver nitrate (11 mg,0.06 mmol), 4,4′,4″-tri-tert-butyl-2,2′:6′,2″-terpyridine (25 mg, 0.06mmol) and iodobenzene diacetate (375 mg, 1.17 mmol) were added to asolution of3-(2,6-difluoro-phenylmethanesulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole(200 mg, 0.8 mmol) in acetonitrile (5 ml) under nitrogen and theresulting dark red solution was stirred for 12 hours at roomtemperature, then heated for 5 min in a sealed tube to 100° C. in themicrowave. The resulting pale yellow solution was concentrated and thecrude product was purified by chromatography on silica gel (eluent:hexane/ethyl acetate) to give3-{2,6-difluoro-phenyl-methane(N-[4-nitrophenylsulphonyl]sulfiliminyl)-5,5-dimethyl-4,5-dihydroisoxazoleas white solid (107 mg, 25% yield).

The compounds mentioned in the following table 65 below can be preparedin analogous manner. One of the compounds (1.18) in Table 65 wasprepared by a different route as given in Example P19.

Example P19 Preparation of3-{2,6-difluoro-phenylmethane(N-ethoxycarbonylmethyl)-sulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole

To a stirred suspension of sodium hydride (80% in mineral oil) (25 mg,0.83 mmol) in dimethoxyethane (3 ml) was added3-{2,6-difluoro-phenylmethanesulfoximinyl)-5,5-dimethyl-4,5-dihydroisoxazole(Compound No. 1.01 of Table 65) (200 mg, 0.69 mmol) as solution indimethoxyethane (1.5 ml) at room temperature under nitrogen. After 5 minhexadecyltributyl phosphonium bromide (phase transfer catalyst, P.T.C.)(21 mg, 0.04 mmol) and ethyl bromoacetate (0.09 ml, 0.83 mmol) wereadded dropwise. After 2 h the mixture was poured into water (5 ml) andextracted several times with ethyl acetate. The combined organic phaseswere dried over MgSO₄ and concentrated. Purification by chromatographyon silica gel (eluent: hexane/ethyl acetate) gave the product (CompoundNo. 1.18 of Table 65) as a yellow gum (103 mg, 40% yield). TABLE 65Compounds of formula Id (Id)

M.p. ¹H-NMR (400 MHz, Nr. R m R⁵ R⁶ Q n [° C.] CDCl₃) 1.01 2,6-F 1 H H H1 89-91 1.45 (s, 3H, Me), 1.55 (s, 3H, Me), 2.9 (d, 1H, CH₂), 3.1 (d,1H, CH₂), 3.28 (broad s, 1H, NH), 4.65 (d, 1H, CH₂), 4.80 (d, 1H, CH₂),7.0 (m, 2H, CH), 7.4 (m, 1H, CH). 1.02 2,6-F 1 Cl H H 1 100 1:1 mixtureof diastereomers: 1.42 (s, 3H, Me), 1.47 (s, 3H, Me), 1.52 (s, 3H, Me),1.57 (s, 3H, Me), 2.95 (d, 1H, CH₂), 3.15 (d, 1H, CH₂), 3.2 (d, 1H,CH₂), 3.3 (d, 1H, CH₂), 3.53 (broad s, 1H, NH), 3.6 (broad s, 1H, NH),6.42 (s, 1H, CHC1), 6.62 (s, 1H, CHCl), 7.02 (m, 4H, CH), 7.45 (m, 2H,CH). 1.03 2,6-F 1 H H —CO(4- 1 154-156 1.55 (s, 6H, Me), 3.15 (d, ClPh)1H, CH₂), 3.35 (d, 1H, CH₂), 5.0 (d, 1H, CH₂), 5.15 (d, 1H, CH₂), 7.02(t, 2H, CH), 7.38 (d, 2H, CH), 7.45 (m, 1H, CH), 8.0 (d, 2H, CH). 1.042,6-F 1 H H —COCF₃ 1 143-144 1.55 (s, 6H, Me), 3.05 (d, 1H, CH₂), 3.25(d, 1H, CH₂), 4.95 (d, 1H, CH₂), 5.2 (d, 1H, CH₂), 7.05 (m, 2H, CH), 7.5(m, 1H, CH). 1.05 2,6-F 1 Cl H —COCF₃ 1 1.60 (s, 6H, Me), 3.25 (d, 1H,CH₂), 3.45 (d, 1H, CH₂), 6.9 (m, 1H, CHCl), 7.05 (m, 2H, CH), 7.52 (m,1H, CH). 1.06 2,6-F 1 H H —(CO)O^(t)Bu 1 1.48-1.52 (m, 15H, Me), 3.0 (d,1H, CH₂), 3.1 (d, 1H, CH₂), 4.8 (d, 1H, CH₂), 5.0 (d, 1H, CH₂), 7.0 (m,2H, CH), 7.4 (m, 1H, CH). 1.07 2,6-F 1 H H —COCH₃ 1 1.45 (s, 3H, Me),1.55 (s, 3H, Me), 2.2 (s, 3H, Me), 3.05 (d, 1H, CH₂), 3.25 (d, 1H, CH₂),4.85 (d, 1H, CH₂), 5.05 (d, 1H, CH₂), 7.0 (m, 2H, CH), 7.4 (m, 1H, CH).1.08 2,6-F 1 H H —CH₃ 1 1.45 (s, 3H, Me), 1.55 (s, 3H, Me), 2.85 (s, 3H,Me), 2.85 (d, 1H, CH₂), 3.05 (d, 1H, CH₂), 4.55 (d, 1H, CH₂), 4.75 (d,1H, CH₂), 7.0 (m, 2H, CH), 7.4 (m, 1H, CH). 1.09 2,6-F 0 H H —COCF₃ 11.5 (s, 6H, Me), 3.0 (d, 1H, CH₂), 3.2 (d, 1H, CH₂), 4.65 (d, 1H, CH₂),4.85 (d, 1H, CH₂), 7.0 (m, 2H, CH), 7.45 (m, 1H, CH). 1.10 2,6-F 1 H H—Si(CH₃)₃ 1 0.8 (s, 9H, Me), 1.5 (s, 6H, Me), 3.0 (d, 1H, CH₂), 3.1 (d,1H, CH₂), 4.65 (s, 2H, CH₂), 7.0 (m, 2H, CH), 7.4 (m, 1H, CH). 1.112,6-F 1 H H —SO₂(4- 1 1.55(s, 6H, Me), 3.25 (d, NO₂Ph) 1H, CH₂), 3.35(d, 1H, CH₂), 4.95 (d, 1H, CH₂), 5.1 (d, 1H, CH₂), 7.05 (m, 2H, CH), 7.5(m, 1H, CH), 8.15 (m, 2H, CH), 8.35 (m, 2H,CH). 1.12 2,6-F 1 H H —SO₂Me1 1.50 (s, 3H, Me), 1.6 (s, 3H, Me), 3.1 (s, 3H, Me), 3.1 (d, 1H, CH₂),3.3 (d, 1H, CH₂), 4.9 (d, 1H, CH₂), 5.0 (d, 1H, CH₂), 7.0 (m, 2H, CH),7.45 (m, 1H, CH). 1.13 2,6-F 1 H H —CHO 1 1.50 (s, 6H, Me), 3.1 (d, 1H,CH₂), 3.25 (d, 1H, CH₂), 5.0 (d, 1H, CH₂), 5.1 (d, 1H, CH₂), 7.02 (m,2H, CH), 7.45 (m, 1H, CH), 8.4 (s, 1H, CHO). 1.14 2,6-F 1 H H —SO₂CF₃ 1108 1.57 (s, 3H, Me), 1.59 (s, 3H, Me), 3.15 (d, 1H, CH₂), 3.25 (d, 1H,CH₂), 5.05 (d, 1H, CH₂), 5.15 (d, 1H, CH₂), 7.05 (m, 2H, CH), 7.5 (m,1H, CH). 1.15 2,6-F 1 H H —NO₂ 1 1.5 (s, 3H, Me), 1.6 (s, 3H, Me), 3.1(d, 1H, CH₂), 3.3 (d, 1H, CH₂), 5.05 (s, 2H, CH₂), 7.05 (m, 2H, CH), 7.5(m, 1H, CH). 1.16 2,6-F 1 H H

1 1.45 (s, 3H, Me), 1.5 (s, 3H, Me), 2.95 (d, 1H, CH₂), 3.3 (d, 1H,CH₂), 5.1 (d, 1H, CH₂), 5.18 (d, 1H, CH₂), 7.0 (m, 2H, CH), 7.2 (d, 1H,CH), 7.4-7.5 (m, 1H, CH), 8.7 (d, 1H, CH). 1.17 2,6-F 1 H H —(CO)OCH₂ 11:1 mixture of ClCH₃ diastereoisomers: 1.5 (s, 6H, Me), 1.52 (s, 3H,Me), 1.55 (s, 3H, Me), 1.7 (s, 3H, Me), 1.75 (s, 3H, Me), 3.0 (d, 1H,CH₂), 3.03 (d, 1H, CH₂), 3.18 (d, 1H, CH₂), 3.2 (d, 1H, CH₂), 4.95 (d,1H, CH₂), 5.0 (d, 1H, CH₂), 5.05 (d, 1H, CH₂), 5.1 (d, 1H, CH₂), 6.5 (q,2H, CH), 7.0-7.1 (m, 4H, CH), 7.4- 7.5 (m, 2H, CH). 1.18 2,6-F 1 H H—CH₂(CO)O 1 1.25 (t, 3H, Me), 1.48 (s, CH₂CH₃ 3H, Me), 1.5 (s, 3H, Me),2.95 (d, 1H, CH₂), 3.1 (d, 1H, CH₂), 3.95 (s, 2H, CH₂), 4.2 (q, 2H,CH₂), 4.75 (d, 1H, CH₂), 4.8 (d, 1H, CH₂), 6.95-7.0 (m, 2H, CH),7.35-7.4 (m, 1H, CH). 1.19 2,6-F 1 H —CH₃ —COCF₃ 1 Diastereomer A: 1.54(s, 3H, Me), 1.57 (s, 3H, Me), 2.02 (d, 3H, Me), 3.06 (d, 1H, CH₂), 3.31(d, 1H, CH₂), 5.43 (q, 1H, CHMe), 7.00 (m, 2H, CH), 7.43 (m, 1H, CH).1.20 2,6-F 1 H —CH₃ —COCF₃ 1 Diastereomer B: 1.36 (s, 3H, Me), 1.48 (s,3H, Me), 2.02 (d, 3H, Me), 2.67 (d, 1H, CH₂), 3.12 (d, 1H, CH₂), 5.35(q, 1H, CHMe), 7.00 (m, 2H, CH), 7.43 (m, 1H, CH). 1.21 2,6-F 1 H H

1 1.55 (s, 3H, Me), 1.57 (s, 3H, Me), 3.15 (d, 1H, CH₂), 3.35 (d, 1H,CH₂), 5.05 (d, 1H, CH₂), 5.2 (d, 1H, CH₂), 7.0-7.05 (m, 2H, CH), 7.3(dd, 1H, CH), 7.4-7.5 (m, 1H, CH), 8.2 (dd, 1H, CH), 8.45 (dd, 1H, CH).1.22 2,6-F 1 F F H 1 112 1.52 (s, 3H, Me), 1.55 (s, 3H, Me), 3.15 (d,1H, CH₂), 3.26 (d, 1H, CH₂), 3.6 (broad s, 1H, NH), 7.05 (t, 2H, CH),7.5-7.6 (m, 1H, CH). 1.23 2,6-F 1 H H

1 1.48 (s, 3H, Me), 1.52 (s, 3H, Me), 3.1 (d, 1H, CH₂), 3.2 (d, 1H,CH₂), 5.1 (d, 1H, CH₂), 5. 15 (d, 1H, CH₂), 7.0-7.05 (m, 2H, CH),7.4-7.5 (m, 1H, CH), 8.2 (d, 1H, CH), 8.25 (d, 1H, CH). 1.24 2-OCF₃ 1 HH H 1 1.4 (s, 3H, Me), 1.45 (s, 3H, Me), 2.9 (d, 1H, CH₂), 3.0 (d, 1H,CH₂), 2.9-3.1 (broad s, 1H, NH), 4.7 (d, 1H, CH₂), 4.78 (d, 1H, CH₂),7.3-7.4 (m, 2H, CH), 7.4- 7.5 (m, 1H, CH), 7.5-7.6 (m, 1H, CH). 1.25 2-1 H H H 1 1.4 (s, 6H, Me), 2.9 (d, 1H, OCHF₂ CH₂), 3.05 (d, 1H, CH₂),4.72 (d, 1H, CH₂), 4.8 (d, 1H, CH₂), 6.6 (t, 1H, CH), 7.2-7.3 (m; 2H,CH), 7.4- 7.45 (m, 1H, CH), 7.55-7.6 (m, 1H, CH). 1.26 2-SCF₃ 1 H H H 11.4 (s, 3H, Me), 1.45 (s, 3H, Me), 2.9 (d, 1H, CH₂), 3.05 (d, 1H, CH₂),5.0 (d, 1H, CH₂), 5.08 (d, 1H, CH₂), 7.5-7.6 (m, 2H, CH), 7.65 (d, 1H,CH), 7.85 (d, 1H, CH). 1.27 2-CH₃ 1 H H H 1 1.4 (s, 3H, Me), 1.45 (s,3H, Me), 2.5 (s, 3H, Me), 2.65 (d, 1H, CH₂), 2.95 (d, 1H, CH₂), 4.7 (d,1H, CH₂), 4.85 (d, 1H, CH₂), 7.2-7.35 (m, 3H, CH), 7.4 (d, 1H, CH). 1.282,6-F, 1 H H H 1 1.5 (s, 3H, Me), 1.51 (s, 3H, 3-CH₃ Me), 2.25 (s, 3H,Me), 3.0 (d, 1H, CH₂), 3.08 (d, 1H, CH₂), 4.7 (d, 1H, CH₂), 4.75 (d, 1H,CH₂), 6.9 (m, 1H, CH), 7.2-7.3 (m, 1H, CH). 1.29 2,3-F 1 H H H 1 1.48(s, 3H, Me), 1.5 (s, 3H, Me), 2.95 (d, 1H, CH₂), 3.05 (d, 1H, CH₂),2.9-3.1 (broad s, 1H, NH), 4.7 (d, 1H, CH₂), 4.75 (d, 1H, CH₂), 7.1-7.3(m, 3H, CH). 1.30 2,4-F 1 H H H 1 1.48 (s, 3H, Me), 1.5 (s, 3H, Me),2.95 (d, 1H, CH₂), 3.05 (d, 1H, CH₂), 4.65 (d, 1H, CH₂), 4.7 (d, 1H,CH₂), 6.9-7.0 (m, 2H, CH), 7.5- 7.55 (m, 1H, CH). 1.31 2-CF₃ 1 H H H 11.4 (s, 3H, Me), 1.45 (s, 3H, Me), 2.9 (d, 1H, CH₂), 3.05 (d, 1H, CH₂),3.4-3.7 (broad s, 1H, NH), 4.9 (d, 1H, CH₂), 4.95 (d, 1H, CH₂), 7.55 (t,1H, CH), 7.65 (t, 1H, CH), 7.75 (d, 1H, CH), 7.85 (d, 1H, CH). 1.32 2-F,1 H H H 1 1.55 (s, 6H, Me), 3.1 (d, 6-CF₃ 1H, CH₂), 3.15 (d, 1H, CH₂),5.05 (d, 1H, CH₂), 5.08 (d, 1H, CH₂), 7.35-7.4 (m, 1H, CH), 7.5-7.6 (m,2H, CH). 1.33 2-Ph 1 H H H 1 1.4 (s, 3H, Me), 1.41 (s, 3H, Me), 2.7 (d,1H, CH₂), 2.85 (d, 1H, CH₂), 3.1-3.3 (broad s, 1H, NH), 4.7 (d, 1H,CH₂), 4.8 (d, 1H, CH₂), 7.35-7.5 (m, 8H, CH), 7.7 (d, 1H, CH). 1.342,5-F 1 H H H 1 1.48 (s, 3H, Me), 1.49 (s, 3H, Me), 2.95 (d, 1H, CH₂),3.05 (d, 1H, CH₂), 4.65 (s, 2H, CH₂), 7.1-7.15 (m, 2H, CH), 7.2-7.3 (m,1H, CH). 1.35 2,6-F 1 H F —COPh 1 128 1.6 (s, 6H, Me) 3.3 (d, 1H, CH₂),3.6 (d, 1H, CH₂), 7.05-7.1 (m, 2H, CH), 7.25 (d, 1H, CH), 7.35-7.40 (m,2H, CH), 7.5-7.6 (m, 2H, CH), 8.0 (d, 2H, CH). 1.36 2,6-F 1 H H —COPh 1141 1.53 (s, 3H, Me), 1.54 (s, 3H, Me), 3.15 (d, 1H, CH₂), 3.4 (d, 1H,CH₂), 5.0 (d, 1H, CH₂), 5.15 (d, 1H, CH₂), 7.0-7.05 (m, 2H, CH),7.35-7.45 (m, 3H, CH), 7.5-7.53 (m, 1H, CH), 8.1 (d, 2H, CH). 1.37 2,6-F1 F F —COPh 1 1.55 (s, 6H, Me), 3.2 (d, 1H, CH₂), 3.32 (d, 1H, CH₂),7.05-7.1 (m, 2H, CH), 7.3 8-7.42 (m, 2H, CH), 7.5-7.55 (m, 1H, CH), 7.55-7.65 (m, 1H, CH), 8.03 (d, 2H, CH). 1.38 2,6-F 1 F F —CO(4- 1 159 1.6(s, 6H, Me), 3.2 (d, 1H, NO₂Ph CH₂), 3.39 (d, 1H, CH₂), 7.1-7.15 (m, 2H,CH), 7.6- 7.7 (m, 1H, CH), 8.2 (d, 2H, CH), 8.25 (d, 2H, CH). 1.39 2-F 1H H H 1 1.38 (s, 3H, Me), 1.42 (s, 3H, Me), 2.85 (d, 1H, CH₂), 3.1 (d,1H, CH₂), 4.95 (d, 1H, CH₂), 5.0 (d, 1H, CH₂), 7.08-7.2 (m, 2H, CH),7.38- 7.43 (m, 2H, CH). 1.40 3,5-F 1 H H H 1 1.43 (s, 3H, Me), 1.48 (s,3H, Me), 2.7-2.9 (broad s, 1H, NH), 2.85 (d, 1H, CH₂), 3.0 (d, 1H, CH₂),4.55 (d, 1H, CH₂), 4.65 (d, 1H, CH₂), 6.85-6.9 (m, 1H, CH), 6.97-7.02(m, 2H, CH). 1.41 2-CN 1 H H H 1 127 1.48 (s, 6H, Me), 3.1 (s, 2H, CH₂),3.05-3.2 (broad s, 1H, NH), 4.85 (s, 2H, CH₂), 7.5-7.55 (m, 1H, CH),7.65- 7.7 (m, 1H, CH), 7.7-7.75 (m, 2H, CH). 1.42 H 1 H H H 1 87 1.45(s, 3H,Me), 1.53 (s, 3H, Me), 2.62 (d, 1H, CH₂), 2.9 (d, 1H, CH₂),3.1-3.18 (broad s, 1H, NH), 4.55 (d, 1H, CH₂), 4.68 (d, 1H, CH₂),7.4-7.5 (m, SH, CH). 1.43 2,6-F 1 H F —CO(4- 1 159 1.6 (s, 6H, Me), 3.3(d, 1H, ClPh) CH₂), 3.57 (d, 1H, CH₂), 7.05-7.1 (m, 2H, CH), 7.2 (d, 1H,CH), 7.35 (d, 2H, CH), 7.5-7.6 (m, 1H, CH), 7.9 (d, 2H, CH). 1.44 2,6-F1 F F —CO(4- 1 1.6 (s, 6H, Me), 3.2 (d, 1H, ClPh) CH₂), 3.5 (d, 1H,CH₂), 7.1 (t, 2H, CH), 7.38 (d, 2H, CH), 7.58-7.65 (m, 1H, CH), 7.95 (d,2H, CH). 1.45 2,6-F 1 H H —CO(4- 1 164 1.55 (s, 6H, Me), 3.15 (d, NO₂Ph)1H, CH₂), 3.4 (d, 1H, CH₂), 5.0 (d, 1H, CH₂), 5.15 (d, 1H, CH₂),7.0-7.05 (m, 2H, CH), 7.4-7.5 (m, 1H, CH), 8.23 (s, 4H, CH). 1.46 2-F,4-1 H H H 1 1.45 (s, 6H, Me), 2.8-3.0 (CO)O (broad s, 1H, NH), 2.95 (d,CH₃ 1H, CH₂), 3.05 (d, 1H, CH₂), 3.95 (s, 3H, Me), 4.73 (s, 2H, CH₂),7.6 (t, 1H, CH), 7.8 (d, 1H, CH), 7.9 (d, 1H, CH). 1.47 2-F,4- 1 H H H 1125 1.4 (t, 3H, Me), 1.48 (s, 6H, (CO) Me), 2.6-2.9 (broad s, 1H, OC₂H₅NH), 2.95 (d, 1H, CH₂), 3.05 (d, 1H, CH₂), 4.4 (q, 2H, CH₂), 4.72 (s,2H, CH₂), 7.6 (t, 1H, CH), 7.8 (d, 1H, CH), 7.9 (d, 1H, CH). 1.48 2,3- 1H H H 1 126 1.45 (s, 6H, Me), 2.95 (d, OCH₂ 1H, CH₂), 3.05 (d, 1H,OCH₂-, CH₂), 3.2-3.4 (broad s, 1H, 5-F NH), 4.63 (d, 1H, CH₂), 4.68 (d,1H, CH₂), 4.88 (s, 2H, CH₂), 5.25 (s, 2H, CH₂), 6.75 (dd, 1H, CH), 7.1(dd, 1H, CH). 1.49 2,3- 1 H H —COCF₃ 1 1.5 (s, 3H, Me), 1.51 (s, 3H,OCH₂ Me), 2.95 (d, 1H, CH₂), OCH₂-, 3.18 (d, 1H, CH₂), 4.9 (s, 5-F 2H,CH₂), 5.0 (s, 2H, CH₂), 5.32 (d, 1H, CH₂), 5.37 (d, 1H, CH₂), 6.82 (dd,1H, CH), 7.05 (dd, 1H, CH). 1.50 2,6-F 1 H F —CO(4- 1 Diastereomer A:1.6 (s, 6H, NO₂Ph) Me), 3.32 (d, 1H, CH₂), 3.6 (d, 1H, CH₂), 7.1-7.15(m, 2H, CH), 7.2 (d, 1H, CH), 7.55-7.65 (m, 1H, CH), 8.12 (d, 2H, CH),8.33 (d, 2H, CH). 1.51 2,6-F 1 H F —CO(4- 1 Diastereomer B: 1.48 (s,NO₂Ph) 3H, Me), 1.52 (s, 3H, Me), 3.15 (d, 1H, CH₂), 3.3 (d, 1H, CH₂),6.85 (d, 1H, CH), 6.95-7.05 (m, 2K, CH), 7.45-7.5 (m, 1H, CH), 8.13 (d,2H, CH), 8.17 (d, 2H, CH). 1.52 2,6-F 1 H F H 1 Diastereomer A: 1.55 (s,6H, Me) 3.22 (d, 1H, CH₂), 3.3 (d, 1H, CH₂), 3.4 (broad s, 1H, Nh), 6.9(d, 1H, CH), 7.0-7.1 (m, 2H, CH), 7.45-7.55 (m, 1H, CH). 1.53 2,6-F 1 HF H 1 Diastereomer B: 1.55 (s, 6H, Me) 3.15 (d, 1H, CH₂), 3.22 (d, 1H,CH₂), 3.4 (broad s, 1H, NH), 6.65 (d, 1H, CH), 7.0-7.05 (m, 2H, CH),7.45-7.55 (m, 1H, CH). 1.54 2,6-F 1 Cl F H 1 Diastereomer A: 1.5 (s, 3H,Me), 1.55 (s, 3H, Me), 3.2 (d, 1H, CH₂), 3.28 (d, 1H, CH₂), 3.85 (broads, 1H, NH), 7.0 (t, 2H, CH), 7.45- 7.52 (m, 1H, CH). 1.55 2,6-F 1 Cl F H1 Diastereomer B: 1.5 (s, 3H, Me), 1.52 (s, 3H, Me), 3.02 (d, 1H, CH₂),3.25 (d, 1H, CH₂), 3.65 (broad s, 1H, NH), 7.05 (t, 2H, CH), 7.45-7.55(m, 1H, CH). 1.56 2- 1 H F H 1 4:1 mixture of OCF₃ diastereomers (notseparated) major isomer: 1.5 (s, 3H, Me), 1.55 (s, 3H, Me), 3.1 (d, 1H,CH₂), 3.12 (d, 1H, CH₂), 3.2-3.3 (broad s, 1H, NH), 6.7 (d, 1H, CH),7.38- 7.45 (m, 2H, CH), 7.6 (t, 1H, CH), 7.8 (d, 1H, CH). minor isomer:1.5 (s, 3H, Me), 1.55 (s, 3H, Me), 3.2- 3.3 (m, 3H, CH₂ & NH), 6.9 (d,1H, CH), 7.38-7.45 (m, 2H, CH), 7.6 (t, 1H, CH), 7.65 (d, 1H, CH). 1.572- 1 F F H 1 1.52 (s, 3H, Me), 1.55 (s, OCF₃ 3H, Me), 3.15 (d, 1H, CH₂),3.28 (d, 1H, CH₂), 3.5 (broad s, 1H, NH), 7.45- 7.52 (m, 2H, CH), 7.67-7.72 (m, 1H, CH), 7.75 (d, 1H, CH). 1.58 2- 1 H H —COCF₃ 1 1.43 (t, 3H,Me), 1.51 (s, Cl, 3- 3H, Me), 1.55 (s, 3H, Me), (CO) 3.08 (d, 1H, CH₂),3.23 (d, OC₂H 1H, CH₂), 3.38 (s, 3H, Me), 5,6- 4.46 (q, 2H, CH₂), 5.22(d, SO₂C 1H, CH₂), 6.01 (d, 1H, H₃ CH₂), 7.95 (d, 1H, CH), 8.15 (d, 1H,CH). 1.59 2- 1 H H H 1 44-47 1.41 (t, 3H, Me), 1.54 (s, Cl,3- 6H, Me),3.17 (s, 2H, CH₂), (CO) 3.38 (s, 3H, Me), 4.45 (q, OC₂H₅, 2H, CH₂), 5.80(broad s, 6-SO₂C 2H, CH₂), 7.86 (d, 1H, CH), H₃ 8.14 (d, 1H, CH).Key:Me = methyl;s = singlet;m = multiplet;d = doublet;dd = double doublet;t = triplet;q = quartet.

TABLE 66 Compounds of formula Ie (Ie)

M.p. ¹H-NMR (400 MHz, Nr. m R⁵ R⁶ Q R¹⁷ R¹⁸ R¹⁹ n [° C.] CDCl₃) 2.01 1 HH H CH₃ CF₃ Cl 1 101- 1.50 (s, 6H, Me), 2.3 103 (broad s, 1H, NH), 3.0(d, 1H, CH₂), 3.2 (d, 1H, CH₂), 3.8 (s, 3H, Me), 4.60 (d, 1H, CH₂), 4.7(d, 1H, CH₂). 2.02 1 H H —COCF₃ CH₃ CF₃ Cl 1 1.55 (s, 6H, Me), 3.15 (d,1H, CH₂), 3.35 (d, 1H, CH₂), 3.94 (s, 3H, Me), 4.22 (s, 2H, CH₂). 2.03 1F F H CH₃ CF₃ Cl 1 1.52 (s, 3H, Me), 1.54 (s, 3H, Me), 3.15 (d, 1H,CH₂), 3.25 (d, 1H, CH₂), 3.55 (broad s, 1H, NH), 3.97 (s, 3H, Me). 2.041 H H H CH₃ OCHF₂ CF₃ 1 1.5 (s, 3H, Me), 1.5 (s, 3H, Me), 3.1 (d, 1H,CH₂), 3.1 (d, 1H, CH₂), 3.93 (s, 3H, Me), 4.55 (d, 1H, CH₂), 4.55 (d,1H, CH₂), 6.9 (t, J= 75 Hz, 1H, CH). 2.05 1 H H —COCF₃ CH₃ CF₃ H 1 1.51(s, 3H, Me), 1.52 (s, 3H, Me), 3.07 (d, 1H, CH₂), 3.30 (d, 1H, CH₂),4.00 (s, 3H, Me), 4.94 (s, 2H, CH₂), 7.70 (s, 1H, CH). 2.06 1 H H H CH₃CF₃ H 1 1.44 (s, 3H, Me), 1.47 (s, 3H, Me), 2.98 (d, 1H, CH₂), 3.08 (d,1H, CH₂), 3.97 (s, 3H, Me), 4.56 (d, 1H, CH₂), 4.62 (d, 1H, CH₂), 7.75(s, 1H, CH). 2.07 1 H H H CH₃ CHF₂ H 1 1.43 (s, 3H, Me), 1.46 (s, 3H,Me), 2.99 (d, 1H, CH₂), 3.08 (d, 1H, CH₂), 3.93 (s, 3H, Me), 4.59 (d,1H, CH₂), 4.65 (d, 1H, CH₂), 6.76 (t, 1H, CH), 7.70 (s, 1H, CH). 2.08 1H H —COCF₃ CH₃ CHF₂ H 1 1.50 (s, 3H, Me), 1.51 (s, 3H, Me), 3.00 (d, 1H,CH₂), 3.28 (d, 1H, CH₂), 3.96 (s, 3H, Me), 4.96 (s, 2H, CH₂), 6.76 (t,1H, CH), 7.70 (s, 1H, CH).Key:Me = methyl;s = singlet;d = doublet;t = triplet.

BIOLOGICAL EXAMPLES Example B1 Herbicidal Action

Monocotyledonous and dicotyledonous test plants were sown in sterilisedstandard soil in seed trays each having 96 cells. After one day(pre-emergence) or after 8 to 9 days cultivation (post-emergence) undercontrolled conditions in a climatic chamber (cultivation at 17/23° C.;13 hours light; 50-60% humidity; after application at 19/24° C.), theplants were treated with an aqueous spray solution of 1000 mg/l of theactive ingredient used (including 10% DMSO as solvent). The plants weregrown on in the climatic chamber until the test was evaluated (10=totaldamage to plant, 0=no damage to plant) after 9 or 13 days. TABLE B1Application pre-emergence Comp. No. [g/ha] Digitaria Agrostis PoaSetaria 1.01 1000 10 10 10 9 1.02 1000 10 10 10 10 1.03 1000 8 7 10 81.04 1000 10 10 10 10 1.05 1000 9 10 10 9 1.06 1000 7 9 6 10 1.07 1000 910 10 9 1.08 1000 7 10 10 9 1.13 1000 9 10 10 9 1.14 1000 7 10 10 0 1.151000 9 10 10 8 1.17 1000 8 10 10 8 1.19 1000 9 10 6 9 1.20 1000 8 9 4 81.21 1000 9 10 10 9 1.22 1000 10 10 10 10 1.24 1000 9 10 0 8 1.25 1000 910 10 8 1.27 1000 8 5 0 5 1.28 1000 9 10 10 8 1.29 1000 8 10 10 6 1.301000 10 10 10 8 1.31 1000 8 10 8 8 1.32 1000 10 10 10 9 1.34 1000 9 1010 8 1.35 1000 8 10 10 8 1.36 1000 5 10 0 7 1.48 1000 8 0 0 8 1.56 10009 10 10 8 2.01 1000 10 10 10 10

Example E1 Pre-Emergent Safening Test on Maize

The test plants were sown in seed trays under greenhouse conditions. Astandard earth was used as the culture substrate. In a pre-emergentstage, the herbicides were applied both by themselves and in a mixturewith safeners to the soil surface. The application was carried out withan aqueous suspension of the test substances, prepared from a 25%wettable powder (Example F3, b according to WO 97/34485) or from asuspension concentrate (Example F8 according to WO 97/34485), to achievea field equivalent of 200 1/ha. The tests were evaluated after 14 days(100%=plants completely dead; 0%=no phytotoxic action on the plants).TABLE E1 Safener action on pre-emergent use on maize (Marista) Comp.1.01 Comp. 1.01 Comp. 1.01 WP 25% AW/W WP 25% AW/W WP 25% AW/W 400 200[g/ha] 400 200 [g/ha] 400 200 [g/ha] Comp. 1.01 Benoxacor DichlormidFurilazole WP 25% AW/W WP 25% AW/W EC 250 GA/L WP 5% AW/W 400 200 [g/ha]100 50 [g/ha] 100 50 [g/ha] 100 50 [g/ha] 62.5 67.5 [%] 55 0 [%] 57.57.5 [%] 25 2.5 [%]

1. A compound of formula (I)

wherein R¹ and R² are each independently of the other hydrogen,C₁-C₁₀alkyl, C₁-C₁₀haloalkyl, C₃-C₈cycloalkyl orC₃-C₈cycloalkyl-C₁-C₃alkyl, or R¹ and R² together with the carbon atomto which they are bonded form a C₃-C₇ring, R³ and R⁴ are eachindependently of the other hydrogen, C₁-C₁₀alkyl, C₁-C₁₀haloalkyl,C₃-C₈cycloalkyl-C₁-C₁₀alkyl, C₁-C₆alkoxy-C₁-C₁₀alkyl or C₃-C₈cycloalkyl,or R³ and R⁴ together with the carbon atom to which they are bonded forma C₃-C₇ring, or R¹ with R³ or R⁴ and together with the carbon atoms towhich they are bonded form a C₅-C₈ring, or R² with R³ or R⁴ and togetherwith the carbon atoms to which they are bonded form a C₅-C₈ring; R⁵ andR⁶ are each independently of the other hydrogen, C₁-C₆alkyl,C₃-C₆cycloalkyl, 4,5-dihydropyrazole-CH₂—,C₁-C₆alkylcarbonyloxy-C₂-C₆alkenyl-, C₃-C₆cycloalkylcarbonyl,C₁-C₆alkoxy-C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, cyano,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, pyrrolyl-CH₂—, pyrazolyl-CH₂—,triazolyl-CH₂—, imidazolyl-CH₂—, tetrazolyl-CH₂—, indolyl-CH₂—,indazolyl-CH₂—, benzotriazolyl-CH₂—, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₂-C₆alkenyloxy, C₂-C₆alkynyloxy, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, phenylcarbonyl or phenylcarbonyl substituted byone to three R⁹, or R⁵ and R⁶ are each independently of the otherphenoxycarbonyl or phenoxycarbonyl substituted by one to three R⁹, or R⁵and R⁶ are each independently of the other benzyloxycarbonyl orbenzyloxy-carbonyl substituted by one to three R⁹, or R⁵ and R⁶ are eachindependently of the other nitro, formyl, carboxyl, halogen, azido,thiocyanato, tri(C₁-C₆alkyl)silyl, C₁-C₆alkylcarbonyl-C₁-C₂alkyl,C₁-C₆alkoxycarbonyl-C₁-C₂alkyl, cyano-C₁-C₂alkyl,C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl,di-C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl, C₁-C₆alkoxy-C₁-C₂alkyl,C₁-C₂alkyl-P(O)(OC₁-C₆alkyl)₂, C₁-C₂alkyl-NO₂, mercapto, phenylthio orphenylthio substituted by one to three R⁹, or R⁵ and R⁶ are eachindependently of the other pyridylthio, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl,C₁-C₆haloalkyl-sulfinyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl,C₁-C₆alkylsulfonyl-C₁-C₆alkyl, C₁-C₆alkylsulphonyloxy-C₁-C₆alkyl,benzylsulfonyl or benzylsulfonyl substituted by one to three R⁹, or R⁵and R⁶ are each independently of the other phenylsulfinyl orphenylsulfinyl substituted by one to three R⁹, or R⁵ and R⁶ are eachindependently of the other phenylsulfonyl or phenylsulfonyl substitutedby one to three R⁹, or R⁵ and R⁶ are each independently of the otherhydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, or R⁵ and R⁶ are each independently of the other benzyl orbenzyl substituted by one to three R⁹, or R⁵ and R⁶ are eachindependently of the other benzyloxy or benzyloxy substituted by one tothree R⁹, or R⁵ and R⁶ are each independently of the other—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCHO,—NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl, —NHCOO—C₁-C₆alkyl,—NHCONH—C₁-C₆alkyl, —NHCONH—C₁-C₆haloalkyl, —NHSO₂—C₁-C₆alkyl,—NHSO₂—C₁-C₆haloalkyl, —NHSO₂-phenyl or —NHSO₂-phenyl substituted by oneto three R⁹, or R⁵ and R⁶ are each independently of the other—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by one to three R⁹, or R⁵ and R⁶ are each independently ofthe other —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by one to three R⁹, or R⁵ and R⁶ are eachindependently of the other —CONR⁷R⁸ wherein R⁷ and R⁸ are eachindependently of the other hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, phenyl or phenyl substituted by C₁-C₆haloalkyl, nitro,cyano or by halogen, or R⁷ and R⁸ together form a C₃-C₈alkylene groupwhich optionally contains one oxygen or sulfur atom or one to two aminoor C₁-C₆alkylamino groups, or R⁵ and R⁶ are each independently of theother phenyl or naphthyl, which is optionally substituted by one tothree substituents independently selected from C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,benzyloxycarbonyl or benzyloxycarbonyl substituted by one to three R⁹,nitro, cyano, formyl, carboxyl, halogen, azido, thiocyanato,tri(C₁-C₆alkyl)silyl, mercapto, phenylthio or phenylthio substituted byone to three R⁹, phenylsulfinyl or phenyl-sulfinyl substituted by one tothree R⁹, —SF₅, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆alkyl-SO(NH)—, C₁-C₆alkyl-SO(NCH₃), C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by one to three R⁹, phenylsulfonyl orphenylsulfonyl substituted by one to three R⁹, hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by one to three R⁹, benzyloxy orbenzyloxy substituted by one to three R⁹, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted by one tothree R⁹, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by one to three R⁹, or by —CONR⁷R⁸ wherein R⁷and R⁸ are each independently of the other hydrogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸ together form aC₃-C₈alkylene group which optionally contains one oxygen or sulfur atomor one to two amino or C₁-C₆alkylamino groups, or R⁵ and R⁶ are eachindependently of the other a 5- to 10-membered heterocycle containingone to three nitrogen, oxygen or sulfur atoms, which is optionallybenzo-fused, and which is optionally substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, C₁-C₆-hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,benzyloxycarbonyl or benzyloxycarbonyl substituted by, one to three R⁹,phenylthio or phenylthio substituted by one to three R⁹, phenylsulfinylcar phenyl-sulfinyl substituted by one to three R⁹, nitro, cyano,formyl, carboxyl, halogen, azido, thiocyanato, tri(C₁-C₆alkyl)silyl,mercapto, —SF₅, C₁-C₆alkylthio, C₁-C₆alkyl-sulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,benzylsulfonyl or benzylsulfonyl substituted by one to three R⁹,phenylsulfonyl or phenylsulfonyl substituted by one to three R⁹,hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, benzyloxy or benzyloxy substituted by one to three R⁹,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by one to three R⁹, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted by oneto three R⁹, or by —CONR⁷R⁸ wherein R⁷ and R⁸ are each independently ofthe other hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenylor phenyl substituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, orR⁷ and R⁸ together form a C₃-C₈alkylene group which optionally containsone oxygen or sulfur atom or one to two amino or C₁-C₆alkylamino groups,R⁵ and R⁶ together with the carbon atom to which they are bonded form a3- to 10-membered ring which optionally contains one to three nitrogen,oxygen or sulfur atoms and which is optionally substituted by one tothree substituents independently selected from C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkenyl, halogen, cyano, nitro, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, phenylcarbonyl orphenylcarbonyl substituted by C₁-C₆haloalkyl, nitro, cyano or byhalogen, or R⁵ and R⁶ together with the carbon atom to which they arebonded form a group of the formula C═CH₂, C═CH—C₁-C₆alkyl,C═C(halogen)₂, C═CH—N(C₁-C₆alkyl)₂, C═CH—NH(C₁-C₆alkyl) orC═CH—C₁-C₆alkoxy; m is 0 or 1; n is 0, 1 or 2; Q is hydrogen,C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxycarbonyl,tri(C₁-C₆alkyl)-silylethyloxycarbonyl, C₁-C₆haloalkoxycarbonyl, cyano,C₁-C₆haloalkyl, C₁-C₆-hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆cycloalkylcarbonyl, phenylcarbonyl or phenylcarbonyl substituted byone to three R⁹, or Q is benzylcarbonyl or benzylcarbonyl substituted byone to three R⁹, or Q is pyridylcarbonyl or pyridylcarbonyl substitutedby one to three R⁹, or Q is phenoxycarbonyl or phenoxycarbonylsubstituted by one to three R⁹, or Q is benzyloxycarbonyl orbenzyloxycarbonyl substituted by one to three R⁹, or Q is nitro, formyl,tri(C₁-C₆alkyl)silyl, C₁-C₆alkylcarbonyl-C₁-C₂alkyl,C₁-C₆alkoxy-carbonyl-C₁-C₂alkyl, cyano-C₁-C₂alkyl,C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl,di-C₁-C₆alkylaminocarbonyl-C₁-C₂alkyl, C₁-C₆alkoxy-C₁-C₂alkyl,C₁-C₂alkyl-P(O)—(OC₁-C₆alkyl)₂, C₁-C₂alkyl-NO₂,C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfinyl-C₁-C₆alkyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkylsulfonyl-C₁-C₆alkyl, benzylsulfonyl orbenzylsulfonyl substituted by one to three R⁹, or Q is phenylsulfinyl orphenylsulfinyl substituted by one to three R⁹, or Q is phenylsulfonyl orphenylsulfonyl substituted by one to three R⁹, or Q is benzyl or benzylsubstituted by one to three R⁹, or Q is —CONH—SO₂—C₁-C₆alkyl or—CONH—SO₂—C₁-C₆haloalkyl, or Q is —CONR⁷R⁸ wherein R⁷ and R⁸ are eachindependently of the other hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, phenyl or phenyl substituted by C₁-C₆haloalkyl, nitro,cyano or by halogen, or R⁷ and R⁸ together form a C₃-C₈alkylene groupwhich optionally contains one oxygen or sulfur atom or one to two aminoor C₁-C₆alkyl-amino groups, or Q is phenyl or naphthyl, which isoptionally substituted by one to three substituents independentlyselected from C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, benzyloxycarbonyl orbenzyloxycarbonyl substituted by one to three R⁹, nitro, cyano, formyl,carboxyl, halogen, azido, thiocyanato, tri(C₁-C₆alkyl)silyl, mercapto,phenylthio or phenylthio substituted by one to three R⁹, phenylsulfinylor phenylsulfinyl substituted by one to three R⁹, —SF₅, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆alkyl-SO(NH)—,C₁-C₆alkyl-SO(NCH₃), C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkyl-sulfonyl, benzylsulfonyl or benzylsulfonyl substituted byone to three R⁹, phenylsulfonyl or phenylsulfonyl substituted by one tothree R⁹, hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, benzyloxy or benzyloxy substituted by one to three R⁹,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by one to three R⁹, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted by oneto three R⁹, or by —CONR⁷R⁸ wherein R⁷ and R⁸ are each independently ofthe other hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenylor phenyl substituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, orR⁷ and R⁸ together form a C₃-C₈alkylene group which optionally containsone oxygen or sulfur atom or one to two amino or C₁-C₆alkylamino groups,or Q is a 3- to 10-membered heterocycle containing one or more nitrogen,oxygen or sulfur atoms, which is optionally benzo-fused, and which isoptionally substituted by one to three substituents independentlyselected from C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆-hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, benzyloxycarbonyl orbenzyloxycarbonyl substituted by one to three R⁹, phenylthio orphenylthio substituted by one to three R⁹, phenylsulfinyl orphenylsulfinyl substituted by one to three R⁹, nitro, cyano, formyl,carboxyl, halogen, azido, thiocyanato, tri(C₁-C₆alkyl)silyl, mercapto,—SF₅, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,benzylsulfonyl or benzylsulfonyl substituted by one to three R⁹,phenylsulfonyl or phenylsulfonyl substituted by one to three R⁹,hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, benzyloxy or benzyloxy substituted by one to three R⁹,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by one to three R⁹, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted by oneto three R⁹, or by —CONR⁷R⁵ wherein R⁷ and R⁸ are each independently ofthe other hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenylor phenyl substituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, orR⁷ and R⁸ together form a C₃-C₈alkylene group which optionally containsone oxygen or sulfur atom or one to two amino or C₁-C₆alkylamino groups;and Y is hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, hydroxyl, carboxyl, halogen,azido, thiocyanato, tri(C₁-C₆alkyl)silyl, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, benzylsulfonyl orbenzyl-sulfonyl substituted by one to three R⁹, or Y is phenylsulfonylor phenylsulfonyl substituted by one to three R⁹, or Y is C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyl-oxy,phenoxy or phenoxy substituted by one to three R⁹, or Y is benzyloxy orbenzyloxy substituted by one to three R⁹, or Y is —CONH—SO₂—C₁-C₆alkylor —CONH—SO₂—C₁-C₆haloalkyl, or Y is phenyl, naphthyl ortetrahydronaphthyl, which is optionally substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkoxycarbonyl, benzyloxycarbonyl, nitro, cyano, formyl, carboxyl,halogen, azido, thiocyanato, tri(C₁-C₆alkyl)silyl, mercapto, phenylthio,phenylsulfinyl, —SF₅, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, benzylsulfonyl or benzylsulfonyl substituted by oneto three R⁹, phenylsulfonyl or phenylsulfonyl substituted by one tothree R⁹, hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenoxy or phenoxy substituted by one tothree R⁹, benzyloxy or benzyloxy substituted by one to three R⁹,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl,—NHCO—C₁-C₆haloalkyl, —NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl,—OCO—C₁-C₆alkyl, —OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenylsubstituted by one to three R⁹, —OCONH—C₁-C₆alkyl,—OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or —OCONH-phenyl substituted by oneto three R⁹, or by —CONR⁷R⁸ wherein R⁷ and R⁸ are each independently ofthe other hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenylor phenyl substituted by C₁-C₆haloalkyl, nitro, cyano or by halogen, orR⁷ and R⁸ form a C₃-C₈alkylene group which optionally contains oneoxygen or sulfur atom or one to two amino or C₁-C₆alkylamino groups, orY is a 5- to 10-membered heterocycle containing one to three nitrogen,oxygen or sulfur atoms, which is optionally benzo-fused, and which isoptionally substituted by one to three substituents independentlyselected from C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl,C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, nitro,cyano, formyl, carboxyl, halogen, azido, thiocyanato,tri(C₁-C₆alkyl)silyl, mercapto, —SF₅, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, benzylsulfonyl orbenzylsulfonyl substituted by one to three R⁹, phenylsulfonyl orphenylsulfonyl substituted by one to three R⁹, hydroxyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenoxy or phenoxy substituted by one to three R⁹, benzyloxy orbenzyloxy substituted by one to three R⁹, —CONH—SO₂—C₁-C₆alkyl,—CONH—SO₂—C₁-C₆haloalkyl, —NHCO—C₁-C₆alkyl, —NHCO—C₁-C₆haloalkyl,—NHCO₂—C₁-C₆alkyl, —NHCO₂—C₁-C₆haloalkyl, —OCO—C₁-C₆alkyl,—OCO—C₁-C₆haloalkyl, —OCO-phenyl or —OCO-phenyl substituted by one tothree R⁹, —OCONH—C₁-C₆alkyl, —OCONH—C₁-C₆haloalkyl, —OCONH-phenyl or—OCONH-phenyl substituted by one to three R⁹, or by —CONR⁷R⁹ wherein R⁷and R⁸ are each independently of the other hydrogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl or phenyl substituted byC₁-C₆haloalkyl, nitro, cyano or by halogen, or R⁷ and R⁸ together form aC₃-C₈alkylene group which optionally contains one oxygen or sulfur atomor one to two amino or C₁-C₆alkylamino groups; R⁹ are independently ofeach other C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl,carboxyl or halogen; and to N-oxides, salts and optical isomers ofcompounds of formula I.
 2. A compound as claimed in claim 1 in which R¹,R², R³, R⁴ are each independently hydrogen, methyl, fluoromethyl,chloromethyl, difluoromethyl or trifluoromethyl.
 3. A compound asclaimed in claim 1 in which R¹ and R² are both methyl.
 4. A compound asclaimed in claim 1 in which R³ and R⁴ are both hydrogen.
 5. A compoundas claimed in claim 1 in which R⁵ and R⁶ are independently of each otherhydrogen, fluoro, chloro, methyl, acetyl or methoxycarbonyl.
 6. Acompound as claimed in claim 1 in which R⁵ and R⁶ are independently ofeach, other halogen.
 7. A compound as claimed in claim 1 in which R⁵ andR⁶ are selected from chlorine and fluorine.
 8. A compound as claimed inclaim 7 in which R⁵ and R⁶ are fluorine.
 9. A compound as claimed inclaim 1 in which Q is hydrogen, formyl or acetyl.
 10. A compound asclaimed in claim 5 in which Q is hydrogen.
 11. A compound as claimed inclaim 1 in which m is
 1. 12. A compound as claimed in claim 1 in which nis
 1. 13. A process for the preparation of a compound of formula Iwherein R¹, R², R³, R⁴, R⁵, R⁶, Q and Y are as defined in claim 1, m is1 and n is 1, wherein a compound of formula Ic,

wherein R¹, R², R³, R⁴, Q and Y are as defined in claim 1 and m is 1, isreacted in an inert solvent in the presence of a base in a single stepor stepwise in succession with compounds of formula R⁵−X^(A) and/orR⁵—X^(A), wherein R⁵ and R⁶ are as defined in claim 1 and X^(A) is aleaving group.
 14. A process according to claim 12 wherein R⁵ and/or R⁶are halogen.
 15. A process for the preparation of a compound of formulaI wherein R¹, R², R³, R⁴, R⁵, Q and Y are as defined in claim 1, R⁶ isC₁-C₁₀alkyl or halogen, m is 1 and n is 1, wherein a compound of formulaId,

wherein R¹, R², R³, R⁴, Q and Y are as defined in claim 1, R⁶ isC₁-C₁₀alkyl or halogen and m is 1, is reacted in an inert solvent in thepresence of a base with a compound of formula R⁵—X^(A), wherein R⁵ is asdefined in claim 1 and X^(A) is a leaving group.
 16. A process accordingto claim 15 wherein R⁵ is halogen.
 17. A process for the preparation ofa compound of formula I wherein R¹, R², R³, R⁴, R⁵, Q, n and Y are asdefined in claim 1 and m is 0 or 1, wherein a compound of formula Ia,

wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Y are as defined in claim 1 and mis 0 or 1, is reacted in an inert solvent in the presence of a base witha compound of the formula Q-X^(A), wherein Q is as defined in claim 1and X^(A) is a leaving group.
 18. A process for the preparation of acompound of formula I wherein R¹, R², R³, R⁴, R⁵, Q, n and Y are asdefined in claim 1 and m is 1, wherein a compound of formula Ia,

wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Y are as defined in claim 1 and mis 1, is reacted in an inert solvent with a nitrating agent.
 19. Aprocess for the preparation of a compound of formula Ia wherein R¹, R²,R³, R⁴, R⁵, R⁶, n and Y are as defined in claim 1 and m is 0 or 1,wherein a compound of formula Ib,

wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Y are as defined in claim 1, m is0 or 1 and Q^(A) is an electron withdrawing group, is reacted in aninert solvent with either an acid, or a base, or a suitable nucleophile.20. A process for the preparation of a compound of formula Ib whereinR¹, R², R³, R⁴, R⁵, R⁶, n and Y are as defined in claim 1 and m is 0 or1, wherein a compound of formula II,

wherein R¹, R², R³, R⁴, R⁵, R⁶, n and Y are as defined in claim 1 and mis 0 or 1, is reacted in an inert solvent in the presence of a suitabletransition metal catalyst, with an organic azide or with an iminationreagent of the formula ArI═NQ^(A), wherein Q^(A) is an electronwithdrawing group and Ar is an optionally substituted phenyl.
 21. Aprocess for the preparation of a compound of formula I wherein R¹, R²R³,R⁴, R⁵, R⁶, Q, n and Y are as defined in claim 1 and m is 1, wherein acompound of formula I,

wherein R¹, R², R³, R⁴, R⁵, R⁶, Q, n and Y are as defined in claim 1 andm is 0, is reacted with an oxidant in an inert solvent.
 22. A herbicidalcomposition which comprises a herbicidally effective amount of acompound of formula I in addition to formulation adjuvants.
 23. Acomposition according to claim 22, which comprises a further herbicidein addition to the compound of formula I.
 24. A composition according toclaim 22, which comprises a safener in addition to the compound offormula I.
 25. A method of controlling grasses and weeds in crops ofuseful plants, which comprises applying a herbicidally effective amountof a compound of formula I, or of a composition comprising such acompound, to the plants or to the locus thereof.